DD155061A5 - Verfahren zur einfuehrung von alkylradikalen in kohlenstoffketten mit einer funktionellen gruppe - Google Patents

Verfahren zur einfuehrung von alkylradikalen in kohlenstoffketten mit einer funktionellen gruppe Download PDF

Info

Publication number: DD155061A5
Authority: DD; German Democratic Republic
Prior art keywords: chain; radical; carbon atoms; formula; mol
Prior art date: 1979-12-07

Application number

DD80225836A

Other languages

German (de)

English (en)

Inventor

Michael Bouisset

Michel Chignac

Claude Grain

Charles Pigerol

Original Assignee

Sanofi Sa

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1979-12-07

Filing date

1980-12-08

Publication date

1982-05-12

1980-12-08 Application filed by Sanofi Sa filed Critical Sanofi Sa

1982-05-12 Publication of DD155061A5 publication Critical patent/DD155061A5/de

Links

238000000034 method Methods 0.000 title claims abstract description 110
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 title claims abstract description 23
239000002585 base Substances 0.000 claims abstract description 98
239000000203 mixture Substances 0.000 claims abstract description 93
-1 alkali metal amide Chemical class 0.000 claims abstract description 51
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 30
229910052783 alkali metal Inorganic materials 0.000 claims abstract description 18
125000000524 functional group Chemical group 0.000 claims abstract description 13
150000001340 alkali metals Chemical class 0.000 claims abstract description 9
125000001424 substituent group Chemical group 0.000 claims abstract description 9
239000003960 organic solvent Substances 0.000 claims abstract description 7
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 112
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 95
RFFFKMOABOFIDF-UHFFFAOYSA-N Pentanenitrile Chemical compound CCCCC#N RFFFKMOABOFIDF-UHFFFAOYSA-N 0.000 claims description 59
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 56
101000588924 Anthopleura elegantissima Delta-actitoxin-Ael1a Proteins 0.000 claims description 54
YCBOPMITSGZJDX-UHFFFAOYSA-N 2-propylpentanenitrile Chemical compound CCCC(C#N)CCC YCBOPMITSGZJDX-UHFFFAOYSA-N 0.000 claims description 44
238000002360 preparation method Methods 0.000 claims description 42
NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims description 35
ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical group [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 claims description 32
150000001875 compounds Chemical class 0.000 claims description 28
239000011734 sodium Substances 0.000 claims description 27
229910052708 sodium Inorganic materials 0.000 claims description 25
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 claims description 24
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 24
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 24
NIJJYAXOARWZEE-UHFFFAOYSA-N Valproic acid Chemical compound CCCC(C(O)=O)CCC NIJJYAXOARWZEE-UHFFFAOYSA-N 0.000 claims description 22
229940005605 valeric acid Drugs 0.000 claims description 16
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 15
239000000725 suspension Substances 0.000 claims description 14
MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 claims description 12
150000001350 alkyl halides Chemical class 0.000 claims description 11
239000001257 hydrogen Substances 0.000 claims description 9
229910052739 hydrogen Inorganic materials 0.000 claims description 9
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 8
229910052744 lithium Inorganic materials 0.000 claims description 8
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 6
229910052700 potassium Inorganic materials 0.000 claims description 6
239000011591 potassium Substances 0.000 claims description 6
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 4
239000002253 acid Substances 0.000 claims description 3
AFRJJFRNGGLMDW-UHFFFAOYSA-N lithium amide Chemical compound [Li+].[NH2-] AFRJJFRNGGLMDW-UHFFFAOYSA-N 0.000 claims description 3
150000001450 anions Chemical class 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
150000001347 alkyl bromides Chemical class 0.000 claims 1
150000001348 alkyl chlorides Chemical class 0.000 claims 1
239000003153 chemical reaction reagent Substances 0.000 claims 1
238000011065 in-situ storage Methods 0.000 claims 1
150000003511 tertiary amides Chemical class 0.000 claims 1
125000000217 alkyl group Chemical group 0.000 abstract description 4
125000003710 aryl alkyl group Chemical group 0.000 abstract description 3
230000029936 alkylation Effects 0.000 description 44
238000005804 alkylation reaction Methods 0.000 description 44
CYNYIHKIEHGYOZ-UHFFFAOYSA-N 1-bromopropane Chemical compound CCCBr CYNYIHKIEHGYOZ-UHFFFAOYSA-N 0.000 description 42
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 36
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 33
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 31
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 29
230000015572 biosynthetic process Effects 0.000 description 28
239000012299 nitrogen atmosphere Substances 0.000 description 28
239000000243 solution Substances 0.000 description 25
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 24
238000006243 chemical reaction Methods 0.000 description 24
239000000047 product Substances 0.000 description 23
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 22
238000003756 stirring Methods 0.000 description 22
239000002904 solvent Substances 0.000 description 16
AWAHTDIOUIVENZ-UHFFFAOYSA-N 2,2-dipropylpentanenitrile Chemical compound CCCC(CCC)(CCC)C#N AWAHTDIOUIVENZ-UHFFFAOYSA-N 0.000 description 13
239000010779 crude oil Substances 0.000 description 13
229910052757 nitrogen Inorganic materials 0.000 description 11
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 10
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 10
239000012429 reaction media Substances 0.000 description 10
239000003085 diluting agent Substances 0.000 description 9
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 8
229940093475 2-ethoxyethanol Drugs 0.000 description 8
230000007062 hydrolysis Effects 0.000 description 8
238000006460 hydrolysis reaction Methods 0.000 description 8
150000002825 nitriles Chemical class 0.000 description 8
239000012074 organic phase Substances 0.000 description 8
229910052938 sodium sulfate Inorganic materials 0.000 description 8
235000011152 sodium sulphate Nutrition 0.000 description 8
KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 7
229940073608 benzyl chloride Drugs 0.000 description 7
239000012153 distilled water Substances 0.000 description 7
238000002329 infrared spectrum Methods 0.000 description 7
239000000376 reactant Substances 0.000 description 7
HLVFKOKELQSXIQ-UHFFFAOYSA-N 1-bromo-2-methylpropane Chemical compound CC(C)CBr HLVFKOKELQSXIQ-UHFFFAOYSA-N 0.000 description 6
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
239000008346 aqueous phase Substances 0.000 description 5
239000007795 chemical reaction product Substances 0.000 description 5
229910003002 lithium salt Inorganic materials 0.000 description 5
159000000002 lithium salts Chemical class 0.000 description 5
239000012071 phase Substances 0.000 description 5
150000003254 radicals Chemical class 0.000 description 5
CUGYNXQASYLIDX-UHFFFAOYSA-N 4-methyl-2-(2-methylpropyl)pentanenitrile Chemical compound CC(C)CC(C#N)CC(C)C CUGYNXQASYLIDX-UHFFFAOYSA-N 0.000 description 4
150000001408 amides Chemical class 0.000 description 4
239000012043 crude product Substances 0.000 description 4
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
239000012044 organic layer Substances 0.000 description 4
FBJFTTFFNCTVGR-UHFFFAOYSA-N 2-benzyl-3-phenylpropanenitrile Chemical compound C=1C=CC=CC=1CC(C#N)CC1=CC=CC=C1 FBJFTTFFNCTVGR-UHFFFAOYSA-N 0.000 description 3
ACRWYXSKEHUQDB-UHFFFAOYSA-N 3-phenylpropionitrile Chemical compound N#CCCC1=CC=CC=C1 ACRWYXSKEHUQDB-UHFFFAOYSA-N 0.000 description 3
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
101150103171 DARS1 gene Proteins 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
238000001035 drying Methods 0.000 description 3
150000002500 ions Chemical class 0.000 description 3
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
YAYNEUUHHLGGAH-UHFFFAOYSA-N 1-chlorododecane Chemical compound CCCCCCCCCCCCCl YAYNEUUHHLGGAH-UHFFFAOYSA-N 0.000 description 2
SZNYYWIUQFZLLT-UHFFFAOYSA-N 2-methyl-1-(2-methylpropoxy)propane Chemical compound CC(C)COCC(C)C SZNYYWIUQFZLLT-UHFFFAOYSA-N 0.000 description 2
FZPDOGVFWQQSLF-UHFFFAOYSA-N 4-methyl-2-propylpentanenitrile Chemical compound CCCC(C#N)CC(C)C FZPDOGVFWQQSLF-UHFFFAOYSA-N 0.000 description 2
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
FIPWRIJSWJWJAI-UHFFFAOYSA-N Butyl carbitol 6-propylpiperonyl ether Chemical compound C1=C(CCC)C(COCCOCCOCCCC)=CC2=C1OCO2 FIPWRIJSWJWJAI-UHFFFAOYSA-N 0.000 description 2
BMTAFVWTTFSTOG-UHFFFAOYSA-N Butylate Chemical compound CCSC(=O)N(CC(C)C)CC(C)C BMTAFVWTTFSTOG-UHFFFAOYSA-N 0.000 description 2
UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 2
239000012298 atmosphere Substances 0.000 description 2
208000018300 basal ganglia disease Diseases 0.000 description 2
244000309464 bull Species 0.000 description 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
239000011575 calcium Substances 0.000 description 2
239000001110 calcium chloride Substances 0.000 description 2
229910001628 calcium chloride Inorganic materials 0.000 description 2
238000010411 cooking Methods 0.000 description 2
238000001816 cooling Methods 0.000 description 2
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
206010015037 epilepsy Diseases 0.000 description 2
229910052740 iodine Inorganic materials 0.000 description 2
AHNJTQYTRPXLLG-UHFFFAOYSA-N lithium;diethylazanide Chemical compound [Li+].CC[N-]CC AHNJTQYTRPXLLG-UHFFFAOYSA-N 0.000 description 2
239000002480 mineral oil Substances 0.000 description 2
235000010446 mineral oil Nutrition 0.000 description 2
KYZCGAYOKKRLFZ-UHFFFAOYSA-N n,n-diethyl-2-propylpentanamide Chemical compound CCCC(CCC)C(=O)N(CC)CC KYZCGAYOKKRLFZ-UHFFFAOYSA-N 0.000 description 2
YDNGWBPWLNQCSF-UHFFFAOYSA-N n,n-diethylpentanamide Chemical compound CCCCC(=O)N(CC)CC YDNGWBPWLNQCSF-UHFFFAOYSA-N 0.000 description 2
230000002276 neurotropic effect Effects 0.000 description 2
239000003921 oil Substances 0.000 description 2
CFEYBLWMNFZOPB-UHFFFAOYSA-N pent-4-enenitrile Chemical compound C=CCCC#N CFEYBLWMNFZOPB-UHFFFAOYSA-N 0.000 description 2
229960005235 piperonyl butoxide Drugs 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
239000001632 sodium acetate Substances 0.000 description 2
235000017281 sodium acetate Nutrition 0.000 description 2
239000012312 sodium hydride Substances 0.000 description 2
229910000104 sodium hydride Inorganic materials 0.000 description 2
MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
SCSLUABEVMLYEA-UHFFFAOYSA-N tert-butyl pentanoate Chemical compound CCCCC(=O)OC(C)(C)C SCSLUABEVMLYEA-UHFFFAOYSA-N 0.000 description 2
MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 description 1
VSJZBUJCPNVRET-UHFFFAOYSA-N 2,2-bis(prop-2-enyl)propanedioic acid Chemical compound C=CCC(C(=O)O)(CC=C)C(O)=O VSJZBUJCPNVRET-UHFFFAOYSA-N 0.000 description 1
PLNFUNDCAJHMFD-UHFFFAOYSA-N 2-ethoxyethanol;sodium Chemical compound [Na].CCOCCO PLNFUNDCAJHMFD-UHFFFAOYSA-N 0.000 description 1
WEZFYBVBPAUJAL-UHFFFAOYSA-N 2-ethylpentanenitrile Chemical compound CCCC(CC)C#N WEZFYBVBPAUJAL-UHFFFAOYSA-N 0.000 description 1
OKJQSUPURXTNME-UHFFFAOYSA-N 2-prop-2-enylpent-4-enoic acid Chemical compound C=CCC(C(=O)O)CC=C OKJQSUPURXTNME-UHFFFAOYSA-N 0.000 description 1
JOWXGVNOIKHQRE-UHFFFAOYSA-N 2-propylpent-4-ynenitrile Chemical compound CCCC(C#N)CC#C JOWXGVNOIKHQRE-UHFFFAOYSA-N 0.000 description 1
GDUIKHVVYQQWAP-UHFFFAOYSA-N 2-propyltetradecanenitrile Chemical compound CCCCCCCCCCCCC(C#N)CCC GDUIKHVVYQQWAP-UHFFFAOYSA-N 0.000 description 1
DUJMVKJJUANUMQ-UHFFFAOYSA-N 4-methylpentanenitrile Chemical compound CC(C)CCC#N DUJMVKJJUANUMQ-UHFFFAOYSA-N 0.000 description 1
OSDWBNJEKMUWAV-UHFFFAOYSA-N Allyl chloride Chemical compound ClCC=C OSDWBNJEKMUWAV-UHFFFAOYSA-N 0.000 description 1
102100040141 Aminopeptidase O Human genes 0.000 description 1
108050008333 Aminopeptidase O Proteins 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
HMSZBVWINUSBDQ-UHFFFAOYSA-N CCCC(CC)(CC)C(N)=O Chemical compound CCCC(CC)(CC)C(N)=O HMSZBVWINUSBDQ-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 description 1
101100381997 Danio rerio tbc1d32 gene Proteins 0.000 description 1
101100326757 Drosophila melanogaster Capr gene Proteins 0.000 description 1
101100289061 Drosophila melanogaster lili gene Proteins 0.000 description 1
JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
101100381999 Mus musculus Tbc1d32 gene Proteins 0.000 description 1
JPWSFKPKPZCASO-UHFFFAOYSA-N NC(=O)N.NC(=O)N.[Na] Chemical compound NC(=O)N.NC(=O)N.[Na] JPWSFKPKPZCASO-UHFFFAOYSA-N 0.000 description 1
229910002651 NO3 Inorganic materials 0.000 description 1
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
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208000018737 Parkinson disease Diseases 0.000 description 1
241000786363 Rhampholeon spectrum Species 0.000 description 1
FNYLWPVRPXGIIP-UHFFFAOYSA-N Triamterene Chemical compound NC1=NC2=NC(N)=NC(N)=C2N=C1C1=CC=CC=C1 FNYLWPVRPXGIIP-UHFFFAOYSA-N 0.000 description 1
101150046432 Tril gene Proteins 0.000 description 1
229920000027 Valéron Polymers 0.000 description 1
OCBFFGCSTGGPSQ-UHFFFAOYSA-N [CH2]CC Chemical compound [CH2]CC OCBFFGCSTGGPSQ-UHFFFAOYSA-N 0.000 description 1
SPGVRSNGSKATKH-UHFFFAOYSA-H [Cl-].[Cl-].[Cl-].[Cl-].[Cl-].[Cl-].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+] Chemical compound [Cl-].[Cl-].[Cl-].[Cl-].[Cl-].[Cl-].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+] SPGVRSNGSKATKH-UHFFFAOYSA-H 0.000 description 1
230000002411 adverse Effects 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
230000001773 anti-convulsant effect Effects 0.000 description 1
230000002082 anti-convulsion Effects 0.000 description 1
239000001961 anticonvulsive agent Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
238000003556 assay Methods 0.000 description 1
230000003542 behavioural effect Effects 0.000 description 1
AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
238000009835 boiling Methods 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
229940043232 butyl acetate Drugs 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
230000021523 carboxylation Effects 0.000 description 1
238000006473 carboxylation reaction Methods 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
239000013078 crystal Substances 0.000 description 1
125000000753 cycloalkyl group Chemical group 0.000 description 1
238000010908 decantation Methods 0.000 description 1
UZBQIPPOMKBLAS-UHFFFAOYSA-N diethylazanide Chemical compound CC[N-]CC UZBQIPPOMKBLAS-UHFFFAOYSA-N 0.000 description 1
229950001902 dimevamide Drugs 0.000 description 1
MMQSOEGXVXPNSH-UHFFFAOYSA-N disodioarsanylsodium Chemical compound [Na][As]([Na])[Na] MMQSOEGXVXPNSH-UHFFFAOYSA-N 0.000 description 1
230000000694 effects Effects 0.000 description 1
230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000000605 extraction Methods 0.000 description 1
210000003608 fece Anatomy 0.000 description 1
239000012467 final product Substances 0.000 description 1
238000004508 fractional distillation Methods 0.000 description 1
239000012634 fragment Substances 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
231100001261 hazardous Toxicity 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
239000005457 ice water Substances 0.000 description 1
239000012535 impurity Substances 0.000 description 1
239000010410 layer Substances 0.000 description 1
230000010534 mechanism of action Effects 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
UNFUYWDGSFDHCW-UHFFFAOYSA-N monochlorocyclohexane Chemical compound ClC1CCCCC1 UNFUYWDGSFDHCW-UHFFFAOYSA-N 0.000 description 1
YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 1
FTQWRYSLUYAIRQ-UHFFFAOYSA-N n-[(octadecanoylamino)methyl]octadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(=O)NCNC(=O)CCCCCCCCCCCCCCCCC FTQWRYSLUYAIRQ-UHFFFAOYSA-N 0.000 description 1
IHPHPGLJYCDONF-UHFFFAOYSA-N n-propylacetamide Chemical compound CCCNC(C)=O IHPHPGLJYCDONF-UHFFFAOYSA-N 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
239000000843 powder Substances 0.000 description 1
ZQBVUULQVWCGDQ-UHFFFAOYSA-N propan-1-ol;propan-2-ol Chemical compound CCCO.CC(C)O ZQBVUULQVWCGDQ-UHFFFAOYSA-N 0.000 description 1
229940090181 propyl acetate Drugs 0.000 description 1
NJSJBTVAKUBCKG-UHFFFAOYSA-N propylazanide Chemical compound CCC[NH-] NJSJBTVAKUBCKG-UHFFFAOYSA-N 0.000 description 1
238000000746 purification Methods 0.000 description 1
LMHHRCOWPQNFTF-UHFFFAOYSA-N s-propan-2-yl azepane-1-carbothioate Chemical compound CC(C)SC(=O)N1CCCCCC1 LMHHRCOWPQNFTF-UHFFFAOYSA-N 0.000 description 1
238000000926 separation method Methods 0.000 description 1
235000009518 sodium iodide Nutrition 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
CGRKYEALWSRNJS-UHFFFAOYSA-N sodium;2-methylbutan-2-olate Chemical compound [Na+].CCC(C)(C)[O-] CGRKYEALWSRNJS-UHFFFAOYSA-N 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000012258 stirred mixture Substances 0.000 description 1
KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
229960002447 thiram Drugs 0.000 description 1
HDVXJTYHXDVWQO-UHFFFAOYSA-N valeranone Natural products C1CCC(=O)C2(C)CC(C(C)C)CCC21C HDVXJTYHXDVWQO-UHFFFAOYSA-N 0.000 description 1
OMOMUFTZPTXCHP-UHFFFAOYSA-N valpromide Chemical compound CCCC(C(N)=O)CCC OMOMUFTZPTXCHP-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/30—Preparation of carboxylic acid nitriles by reactions not involving the formation of cyano groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/353—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by isomerisation; by change of size of the carbon skeleton
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C53/00—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen
- C07C53/126—Acids containing more than four carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
- C07F1/04—Sodium compounds

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Engineering & Computer Science (AREA)
Oil, Petroleum & Natural Gas (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Lubricants (AREA)
Catalysts (AREA)
Carbon And Carbon Compounds (AREA)
Pens And Brushes (AREA)
Materials For Medical Uses (AREA)
Manufacture Of Tobacco Products (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)

DD80225836A 1979-12-07 1980-12-08 Verfahren zur einfuehrung von alkylradikalen in kohlenstoffketten mit einer funktionellen gruppe DD155061A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
FR7930039A FR2470758A1 (fr)	1979-12-07	1979-12-07	Procede pour la fixation de groupes alkyles sur une chaine carbonee portant un groupe fonctionnel

Publications (1)

Publication Number	Publication Date
DD155061A5 true DD155061A5 (de)	1982-05-12

Family

ID=9232487

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD80225836A DD155061A5 (de)	1979-12-07	1980-12-08	Verfahren zur einfuehrung von alkylradikalen in kohlenstoffketten mit einer funktionellen gruppe

Country Status (29)

Country	Link
US (1)	US4377533A (ja)
EP (1)	EP0030528B1 (ja)
JP (1)	JPS56127323A (ja)
AT (1)	ATE3845T1 (ja)
AU (1)	AU534464B2 (ja)
BG (1)	BG47196A3 (ja)
BR (1)	BR8008001A (ja)
CA (1)	CA1149409A (ja)
CS (1)	CS221281B2 (ja)
DD (1)	DD155061A5 (ja)
DE (1)	DE3063918D1 (ja)
DK (1)	DK155045C (ja)
ES (1)	ES8200068A1 (ja)
FI (1)	FI72508C (ja)
FR (1)	FR2470758A1 (ja)
GB (1)	GB2066242B (ja)
GR (1)	GR70754B (ja)
HU (1)	HU186374B (ja)
IE (1)	IE51211B1 (ja)
IN (1)	IN152767B (ja)
NO (1)	NO162380B (ja)
NZ (1)	NZ195753A (ja)
OA (1)	OA06677A (ja)
PL (1)	PL129554B1 (ja)
PT (1)	PT72150B (ja)
RO (1)	RO81453B (ja)
SU (1)	SU1299497A3 (ja)
YU (1)	YU42230B (ja)
ZA (1)	ZA807377B (ja)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2517676A1 (fr) *	1981-12-07	1983-06-10	Delalande Sa	Nouveaux derives tetrazoliques substitues en position 5, leur procede de preparation et leur application en therapeutique
EP0137445B1 (en) *	1983-10-11	1990-01-03	Merck & Co. Inc.	Process for c-methylation of 2-methylbutyrates
FR2599737B1 (fr) *	1986-06-10	1989-05-19	Sanofi Sa	Procede pour la fixation de groupes alkyles, alkenyles, cycloalkyles ou aralkyles sur une chaine carbonee portant un groupement fonctionnel
JP2533651B2 (ja) *	1988-09-13	1996-09-11	財団法人相模中央化学研究所	２―オキソ―３―芳香族カルボン酸誘導体の製造方法
US4985402A (en) *	1990-04-25	1991-01-15	International Flavors & Fragrances Inc.	2-Methyl-1-nitrilo-2-methyl -1-hydroxylamino-3-(methoxyphenyl) propane, organoleptic uses thereof and processes for preparing same
EP0632008B1 (en) *	1993-06-01	1998-02-04	Ono Pharmaceutical Co., Ltd.	Pentanoic acid derivatives
ZA96338B (en) *	1995-01-25	1996-10-24	Lonza Ag	Process for the preparation of (1-hydroxycyclohexane)- acetonitrile
US5690862A (en) *	1995-11-01	1997-11-25	Albemarle Corporation	No flash point solvent system containing normal propyl bromide
JP4853987B2 (ja) *	2001-07-09	2012-01-11	日本曹達株式会社	α−置換化合物の製造方法

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2442M (fr)	1962-10-17	1964-04-06	Henry Eugene	L'acide dipropylacétique et ses dérivés en tant que nouveuax médicaments dépresseurs du systeme nerveux central.
US3936490A (en) *	1965-06-01	1976-02-03	Exxon Research And Engineering Company	Process for conducting organonitrile addition reactions
BE815273A (fr)	1974-05-20	1974-11-20		Derives actifs de methylamine
FR2383920A1 (fr)	1977-03-15	1978-10-13	Labaz	Procede de preparation d'un derive d'acetonitrile et derive obtenu par ce procede
FR2383907A1 (fr)	1977-03-15	1978-10-13	Labaz	Procede de preparation de derives de l'acide acetique et derives obtenus par ce procede
US4155929A (en) *	1977-05-25	1979-05-22	Labaz	Process for the preparation of an acetonitrile derivative

1979
- 1979-12-07 FR FR7930039A patent/FR2470758A1/fr active Granted
1980
- 1980-11-25 GR GR63450A patent/GR70754B/el unknown
- 1980-11-26 CS CS808191A patent/CS221281B2/cs unknown
- 1980-11-26 ZA ZA00807377A patent/ZA807377B/xx unknown
- 1980-11-28 IN IN1326/CAL/80A patent/IN152767B/en unknown
- 1980-11-28 AU AU64903/80A patent/AU534464B2/en not_active Ceased
- 1980-12-04 PT PT72150A patent/PT72150B/pt not_active IP Right Cessation
- 1980-12-04 NZ NZ195753A patent/NZ195753A/xx unknown
- 1980-12-04 GB GB8038901A patent/GB2066242B/en not_active Expired
- 1980-12-05 FI FI803793A patent/FI72508C/fi not_active IP Right Cessation
- 1980-12-05 EP EP80870053A patent/EP0030528B1/fr not_active Expired
- 1980-12-05 IE IE2560/80A patent/IE51211B1/en not_active IP Right Cessation
- 1980-12-05 HU HU802971A patent/HU186374B/hu not_active IP Right Cessation
- 1980-12-05 AT AT80870053T patent/ATE3845T1/de not_active IP Right Cessation
- 1980-12-05 PL PL1980228294A patent/PL129554B1/pl unknown
- 1980-12-05 BR BR8008001A patent/BR8008001A/pt unknown
- 1980-12-05 SU SU803213402A patent/SU1299497A3/ru active
- 1980-12-05 ES ES497499A patent/ES8200068A1/es not_active Expired
- 1980-12-05 NO NO803686A patent/NO162380B/no unknown
- 1980-12-05 CA CA000366207A patent/CA1149409A/en not_active Expired
- 1980-12-05 BG BG49892A patent/BG47196A3/xx unknown
- 1980-12-05 DE DE8080870053T patent/DE3063918D1/de not_active Expired
- 1980-12-05 YU YU3088/80A patent/YU42230B/xx unknown
- 1980-12-05 DK DK522080A patent/DK155045C/da not_active IP Right Cessation
- 1980-12-06 RO RO102793A patent/RO81453B/ro unknown
- 1980-12-06 OA OA57270A patent/OA06677A/xx unknown
- 1980-12-08 DD DD80225836A patent/DD155061A5/de not_active IP Right Cessation
- 1980-12-08 JP JP17306380A patent/JPS56127323A/ja active Granted
1981
- 1981-04-03 US US06/250,852 patent/US4377533A/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
PT72150A (en)	1981-01-01
ATE3845T1 (de)	1983-07-15
FR2470758A1 (fr)	1981-06-12
RO81453B (ro)	1983-04-30
HU186374B (en)	1985-07-29
AU6490380A (en)	1981-06-11
NZ195753A (en)	1983-07-15
PT72150B (en)	1981-10-28
FR2470758B1 (ja)	1982-07-02
JPS56127323A (en)	1981-10-06
US4377533A (en)	1983-03-22
FI72508C (fi)	1987-06-08
BR8008001A (pt)	1981-06-23
CA1149409A (en)	1983-07-05
DK522080A (da)	1981-06-08
AU534464B2 (en)	1984-02-02
GR70754B (ja)	1983-03-14
EP0030528A1 (fr)	1981-06-17
IN152767B (ja)	1984-03-31
ES497499A0 (es)	1981-10-16
BG47196A3 (en)	1990-05-15
YU42230B (en)	1988-06-30
EP0030528B1 (fr)	1983-06-22
YU308880A (en)	1983-01-21
RO81453A (ro)	1983-04-29
PL129554B1 (en)	1984-05-31
DK155045B (da)	1989-01-30
NO803686L (no)	1981-06-09
DK155045C (da)	1989-06-26
DE3063918D1 (en)	1983-07-28
GB2066242B (en)	1984-09-26
FI803793L (fi)	1981-06-08
ES8200068A1 (es)	1981-10-16
IE802560L (en)	1981-06-07
CS221281B2 (en)	1983-04-29
GB2066242A (en)	1981-07-08
PL228294A1 (ja)	1981-08-07
IE51211B1 (en)	1986-11-12
OA06677A (fr)	1981-09-30
SU1299497A3 (ru)	1987-03-23
ZA807377B (en)	1982-01-27
NO162380B (no)	1989-09-11
FI72508B (fi)	1987-02-27
JPH0135809B2 (ja)	1989-07-27

Legal Events

Date	Code	Title	Description
1996-03-14	ENJ	Ceased due to non-payment of renewal fee

Publication	Publication Date	Title
EP0574667B1 (de)	1997-06-04	Verfahren zur Herstellung von 2,2,6,6-Tetramethylpiperidin-N-oxyl und in seiner 4-Stellung substituierten Derivaten
DE60132771T2 (de)	2009-02-05	Verfahren zur herstellung von cyclopropylcarbonsäureestern und deren derivaten
DD155061A5 (de)	1982-05-12	Verfahren zur einfuehrung von alkylradikalen in kohlenstoffketten mit einer funktionellen gruppe
DE2805488A1 (de)	1978-08-17	Verfahren zur herstellung einer 2-arylpropionsaeure
EP3655413B1 (de)	2021-08-11	Herstellung von glufosinat durch umsetzung von 3-[n-butoxy(methyl)phosphoryl]-1-cyanopropylacetat zu einer mischung aus n-butyl(3-amino-3-cyanopropyl)-methylphosphinat und (3-amino-3-cyanopropyl)-methylphosphinsäure ammoniumsalz
DE69110455T2 (de)	1996-03-07	Herstellung von in organischen lösungsmitteln löslichen indiumalkoxyden.
EP0918047B1 (de)	2002-04-10	Verfahren zur C-Alkylierung von Malonsäureestern
EP0000140B1 (de)	1980-07-23	Verfahren zur Herstellung von wässrigen Lösungen bzw. feinteiligen wässrigen Dispersionen von Polyenyltriarylphosphoniumsalzen
DE1668425A1 (de)	1971-08-05	Verfahren zur Herstellung von Diorganoantimonacylaten
DE69401368T2 (de)	1997-06-05	Verfahren zur Herstellung von 1,4-Dicyano-2-buten
DE69831471T2 (de)	2006-06-22	Herstellung von Alkalimetall-Cyclopentandienverbindungen, und Herstellung von Zirconocenen mit dieser Verbindung
DD202427A5 (de)	1983-09-14	Verfahren zur herstellung von alpha-halogenalkylamiden
DE69722724T2 (de)	2004-06-03	Verfahren zur Herstellung von N-substituierten Lactamen
DE69214914T2 (de)	1997-02-27	Verfahren zur Herstellung von 4-Amino-3-Fluorobenzotrifluorid
DE60201223T2 (de)	2005-01-27	Verfahren zur Herstellung von 3,4-Dihydroxybenzonitril
DE60202583T2 (de)	2006-03-23	Verfahren zur Herstellung von optisch reinem (R)- oder (S)-Tetrahydrofuranylketon
AT500469B1 (de)	2007-04-15	Verbessertes verfahren zur herstellung von 2,2-dichlorophenylessigsäurealkylestern
DE2729974B2 (de)	1980-12-11	Verfahren zur Herstellung von wäßrigen Lösungen bzw. feinteiligen wäßrigen Dispersionen von Polyenyltriarylphosphoniumsalzen
DE60005613T2 (de)	2004-08-12	Verfahren zur Herstellung von Dimethylcyanamid
DE2065698A1 (de)	1974-12-12	Verfahren zur herstellung von 2isopropyl-6-methyl-4(3h)-pyrimidon
EP0443355B1 (de)	1994-03-09	Verfahren zur Herstellung von wasserfreien Zinndicarboxylatdihalogeniden
DE2204194C3 (de)	1975-10-09	Verfahren zur Herstellung von Allylbromid
DE69310136T2 (de)	1997-10-30	Aliphatische Omega-hydroxy-3-ketonitrile und Verfahren zur Herstellung von aliphatischen Omega-hydroxycarbonsäuren
DE2012272C3 (de)	1974-09-12	Verfahren zur Herstellung von Dithiophosphorsäuren-0,0,S-triestern
DE1643890C (de)	1972-11-16	alpha- Hy droxy-gamma-methy lmercaptobuttersäure-methylsulfonium-halogenide und Verfahren zu ihrer Herstellung