NO811132L - Nytt benzaldehyd-derivat og fremgangsmaate for fremstilling og anvendelse derav - Google Patents

Nytt benzaldehyd-derivat og fremgangsmaate for fremstilling og anvendelse derav

Info

Publication number: NO811132L
Authority: NO; Norway
Prior art keywords: chlorophenyl; formula; radical; addition salt; compound
Prior art date: 1980-04-03

Application number

NO811132A

Other languages

English (en)

Norwegian (no)

Inventor

Raymond Alexander Bowie

Original Assignee

Ici Ltd

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.)

1980-04-03

Filing date

1981-04-02

Publication date

1981-10-05

1981-04-02 Application filed by Ici Ltd filed Critical Ici Ltd

1981-10-05 Publication of NO811132L publication Critical patent/NO811132L/no

Links

238000000034 method Methods 0.000 title claims description 28
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical class O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 title 1
-1 alkyl radical Chemical class 0.000 claims description 25
150000001875 compounds Chemical class 0.000 claims description 23
150000003839 salts Chemical class 0.000 claims description 21
SKCQMBTWYIRYCY-UHFFFAOYSA-N [4-(4-chlorophenyl)phenyl]methanol Chemical compound C1=CC(CO)=CC=C1C1=CC=C(Cl)C=C1 SKCQMBTWYIRYCY-UHFFFAOYSA-N 0.000 claims description 16
238000006243 chemical reaction Methods 0.000 claims description 13
230000015572 biosynthetic process Effects 0.000 claims description 12
NFCOSRCEYMBQCJ-UHFFFAOYSA-N 1-chloro-4-[4-(chloromethyl)phenyl]benzene Chemical compound C1=CC(CCl)=CC=C1C1=CC=C(Cl)C=C1 NFCOSRCEYMBQCJ-UHFFFAOYSA-N 0.000 claims description 10
UXCMNUUPBMYDLJ-UHFFFAOYSA-N 4-(4-chlorophenyl)benzaldehyde Chemical group C1=CC(Cl)=CC=C1C1=CC=C(C=O)C=C1 UXCMNUUPBMYDLJ-UHFFFAOYSA-N 0.000 claims description 9
229910052702 rhenium Inorganic materials 0.000 claims description 9
125000005907 alkyl ester group Chemical group 0.000 claims description 8
229910052739 hydrogen Inorganic materials 0.000 claims description 8
239000001257 hydrogen Substances 0.000 claims description 8
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 7
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 7
230000007062 hydrolysis Effects 0.000 claims description 7
238000006460 hydrolysis reaction Methods 0.000 claims description 7
238000002360 preparation method Methods 0.000 claims description 7
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
238000004519 manufacturing process Methods 0.000 claims description 5
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 4
239000003795 chemical substances by application Substances 0.000 claims description 4
229910052736 halogen Inorganic materials 0.000 claims description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 2
229910052794 bromium Inorganic materials 0.000 claims description 2
239000000460 chlorine Substances 0.000 claims description 2
229910052801 chlorine Inorganic materials 0.000 claims description 2
QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 claims description 2
239000007858 starting material Substances 0.000 claims 2
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 24
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
239000000203 mixture Substances 0.000 description 17
239000002585 base Substances 0.000 description 14
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 14
239000000243 solution Substances 0.000 description 13
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
239000012074 organic phase Substances 0.000 description 10
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 10
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 8
239000000543 intermediate Substances 0.000 description 8
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 8
239000007787 solid Substances 0.000 description 8
FPWNLURCHDRMHC-UHFFFAOYSA-N 4-chlorobiphenyl Chemical group C1=CC(Cl)=CC=C1C1=CC=CC=C1 FPWNLURCHDRMHC-UHFFFAOYSA-N 0.000 description 7
239000002904 solvent Substances 0.000 description 7
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
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 description 6
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
229910002091 carbon monoxide Inorganic materials 0.000 description 6
239000003085 diluting agent Substances 0.000 description 6
239000011734 sodium Substances 0.000 description 6
229910052783 alkali metal Inorganic materials 0.000 description 5
229910000041 hydrogen chloride Inorganic materials 0.000 description 5
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 5
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 4
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
235000019253 formic acid Nutrition 0.000 description 4
VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 4
239000013067 intermediate product Substances 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
229910052708 sodium Inorganic materials 0.000 description 4
239000000126 substance Substances 0.000 description 4
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
239000002253 acid Substances 0.000 description 3
229940073608 benzyl chloride Drugs 0.000 description 3
HRQGCQVOJVTVLU-UHFFFAOYSA-N bis(chloromethyl) ether Chemical class ClCOCCl HRQGCQVOJVTVLU-UHFFFAOYSA-N 0.000 description 3
239000003921 oil Substances 0.000 description 3
239000003208 petroleum Substances 0.000 description 3
238000001953 recrystallisation Methods 0.000 description 3
238000003756 stirring Methods 0.000 description 3
239000000725 suspension Substances 0.000 description 3
GRZHHTYDZVRPIC-UHFFFAOYSA-N (benzyloxy)acetic acid Chemical class OC(=O)COCC1=CC=CC=C1 GRZHHTYDZVRPIC-UHFFFAOYSA-N 0.000 description 2
KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 2
BWLBGMIXKSTLSX-UHFFFAOYSA-N 2-hydroxyisobutyric acid Chemical compound CC(C)(O)C(O)=O BWLBGMIXKSTLSX-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
229910021591 Copper(I) chloride Inorganic materials 0.000 description 2
238000005643 Gatterman-Koch carbonylation reaction Methods 0.000 description 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
150000001299 aldehydes Chemical class 0.000 description 2
230000002456 anti-arthritic effect Effects 0.000 description 2
125000003118 aryl group Chemical group 0.000 description 2
KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 2
UGOFYAXVVVXMQT-UHFFFAOYSA-N clobuzarit Chemical compound C1=CC(COC(C)(C)C(O)=O)=CC=C1C1=CC=C(Cl)C=C1 UGOFYAXVVVXMQT-UHFFFAOYSA-N 0.000 description 2
OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 2
239000006185 dispersion Substances 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
239000004312 hexamethylene tetramine Substances 0.000 description 2
235000010299 hexamethylene tetramine Nutrition 0.000 description 2
150000004678 hydrides Chemical class 0.000 description 2
239000012280 lithium aluminium hydride Substances 0.000 description 2
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
239000012299 nitrogen atmosphere Substances 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
238000010992 reflux Methods 0.000 description 2
229910052701 rubidium Inorganic materials 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 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
235000011121 sodium hydroxide Nutrition 0.000 description 2
239000012258 stirred mixture Substances 0.000 description 2
239000008096 xylene Substances 0.000 description 2
WPWHSFAFEBZWBB-UHFFFAOYSA-N 1-butyl radical Chemical compound [CH2]CCC WPWHSFAFEBZWBB-UHFFFAOYSA-N 0.000 description 1
RVPCSOXIXXTDIG-UHFFFAOYSA-N 2-[[4-(4-chlorophenyl)phenyl]methoxy]-2-phenylbutanoic acid Chemical compound C=1C=CC=CC=1C(CC)(C(O)=O)OCC(C=C1)=CC=C1C1=CC=C(Cl)C=C1 RVPCSOXIXXTDIG-UHFFFAOYSA-N 0.000 description 1
QYCBZFRDGXIZIP-UHFFFAOYSA-N 2-hydroxy-2-phenylbutanoic acid Chemical compound CCC(O)(C(O)=O)C1=CC=CC=C1 QYCBZFRDGXIZIP-UHFFFAOYSA-N 0.000 description 1
LZZYPRNAOMGNLH-UHFFFAOYSA-M Cetrimonium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C LZZYPRNAOMGNLH-UHFFFAOYSA-M 0.000 description 1
238000005727 Friedel-Crafts reaction Methods 0.000 description 1
XYVQFUJDGOBPQI-UHFFFAOYSA-N Methyl-2-hydoxyisobutyric acid Chemical compound COC(=O)C(C)(C)O XYVQFUJDGOBPQI-UHFFFAOYSA-N 0.000 description 1
PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical compound CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 0.000 description 1
101150101537 Olah gene Proteins 0.000 description 1
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
239000003125 aqueous solvent Substances 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
NWCHELUCVWSRRS-UHFFFAOYSA-N atrolactic acid Chemical compound OC(=O)C(O)(C)C1=CC=CC=C1 NWCHELUCVWSRRS-UHFFFAOYSA-N 0.000 description 1
238000010533 azeotropic distillation Methods 0.000 description 1
150000003935 benzaldehydes Chemical class 0.000 description 1
PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
WOWHHFRSBJGXCM-UHFFFAOYSA-M cetyltrimethylammonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCC[N+](C)(C)C WOWHHFRSBJGXCM-UHFFFAOYSA-M 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
239000003638 chemical reducing agent Substances 0.000 description 1
229910052681 coesite Inorganic materials 0.000 description 1
229910052906 cristobalite Inorganic materials 0.000 description 1
239000012043 crude product Substances 0.000 description 1
238000004821 distillation Methods 0.000 description 1
IOLQWGVDEFWYNP-UHFFFAOYSA-N ethyl 2-bromo-2-methylpropanoate Chemical compound CCOC(=O)C(C)(C)Br IOLQWGVDEFWYNP-UHFFFAOYSA-N 0.000 description 1
125000004494 ethyl ester group Chemical group 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000000284 extract Substances 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000012467 final product Substances 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
239000005457 ice water Substances 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
238000011031 large-scale manufacturing process Methods 0.000 description 1
239000007788 liquid Substances 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
UBRWRMHONGHPLV-UHFFFAOYSA-N methyl 2-hydroxy-2-phenylbutanoate Chemical compound COC(=O)C(O)(CC)C1=CC=CC=C1 UBRWRMHONGHPLV-UHFFFAOYSA-N 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
235000010446 mineral oil Nutrition 0.000 description 1
229910052759 nickel Inorganic materials 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
239000003444 phase transfer catalyst Substances 0.000 description 1
UXCDUFKZSUBXGM-UHFFFAOYSA-N phosphoric tribromide Chemical compound BrP(Br)(Br)=O UXCDUFKZSUBXGM-UHFFFAOYSA-N 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
159000000001 potassium salts Chemical class 0.000 description 1
150000003242 quaternary ammonium salts Chemical class 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
239000002002 slurry Substances 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
229910052682 stishovite Inorganic materials 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
229910052905 tridymite Inorganic materials 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
- C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
- C07C59/66—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
- C07C17/16—Preparation of halogenated hydrocarbons by replacement by halogens of hydroxyl groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
- C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
- C07C29/14—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of a —CHO group
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/49—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/56—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds
- C07C45/562—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with nitrogen as the only hetero atom
- C07C45/565—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with nitrogen as the only hetero atom by reaction with hexamethylene-tetramine
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/52—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings
- C07C47/55—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings containing halogen

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Plural Heterocyclic Compounds (AREA)

NO811132A 1980-04-03 1981-04-02 Nytt benzaldehyd-derivat og fremgangsmaate for fremstilling og anvendelse derav NO811132L (no)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB8011377		1980-04-03

Publications (1)

Publication Number	Publication Date
NO811132L true NO811132L (no)	1981-10-05

Family

ID=10512608

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO811132A NO811132L (no)	1980-04-03	1981-04-02	Nytt benzaldehyd-derivat og fremgangsmaate for fremstilling og anvendelse derav

Country Status (11)

Country	Link
EP (1)	EP0037698A1 (fi)
JP (1)	JPS56154429A (fi)
AU (1)	AU6850381A (fi)
DK (1)	DK124781A (fi)
FI (1)	FI811034L (fi)
GB (1)	GB2073177A (fi)
GR (1)	GR81361B (fi)
IL (1)	IL62426A0 (fi)
NO (1)	NO811132L (fi)
PT (1)	PT72781B (fi)
ZA (1)	ZA811764B (fi)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
AU4154799A (en)	1998-06-02	1999-12-20	Arthromics Plc	Compounds which interact with the thyroid hormone receptor for the treatment of fibrotic disease

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB985650A (en) *	1960-09-09	1965-03-10	Imp Smelting Corp Ltd	Novel pentafluorophenyl-substituted alcohols
GB1140748A (en) *	1966-06-23	1969-01-22	Ici Ltd	New carboxylic acid derivatives
GB1499655A (en) *	1974-01-31	1978-02-01	Allen & Hanburys Ltd	Biphenyl derivatives

1981
- 1981-03-05 GB GB8106970A patent/GB2073177A/en not_active Withdrawn
- 1981-03-17 ZA ZA00811764A patent/ZA811764B/xx unknown
- 1981-03-18 AU AU68503/81A patent/AU6850381A/en not_active Abandoned
- 1981-03-19 IL IL62426A patent/IL62426A0/xx unknown
- 1981-03-19 DK DK124781A patent/DK124781A/da unknown
- 1981-03-27 GR GR64516A patent/GR81361B/el unknown
- 1981-03-31 PT PT72781A patent/PT72781B/pt unknown
- 1981-03-31 EP EP81301392A patent/EP0037698A1/en not_active Withdrawn
- 1981-04-02 NO NO811132A patent/NO811132L/no unknown
- 1981-04-03 FI FI811034A patent/FI811034L/fi not_active Application Discontinuation
- 1981-04-03 JP JP4951381A patent/JPS56154429A/ja active Pending

Also Published As

Publication number	Publication date
IL62426A0 (en)	1981-05-20
GR81361B (fi)	1984-12-11
JPS56154429A (en)	1981-11-30
EP0037698A1 (en)	1981-10-14
PT72781A (en)	1981-04-01
AU6850381A (en)	1981-10-08
FI811034L (fi)	1981-10-04
ZA811764B (en)	1982-04-28
DK124781A (da)	1981-10-04
GB2073177A (en)	1981-10-14
PT72781B (en)	1982-03-23

Publication	Publication Date	Title
US4187249A (en)	1980-02-05	Promoting the reaction of sodium salts of formyl derivatives of aromatic amines to form nitrodiarylamines
Bach	1968	Preparation of tertiary N, N-dimethylamines by the leuckart reaction
NO811132L (no)	1981-10-05	Nytt benzaldehyd-derivat og fremgangsmaate for fremstilling og anvendelse derav
CA1208237A (en)	1986-07-22	Process for preparing 6-(lower alkoxy)-5- (trifluoromethyl)-1-naphthalenecarboxylic acid
US4259496A (en)	1981-03-31	Halogenation of pyridine compounds
US4469893A (en)	1984-09-04	Method for the preparation of nitrodiphenyl ethers
IE62753B1 (en)	1995-02-22	Method of preparing 4-disubstituted phenyl-1-tetralones
EP0016504A2 (en)	1980-10-01	Novel trihaloethyl carbonate derivatives and a process for their production
US3424804A (en)	1969-01-28	Preparation of highly fluorinated aromatic compounds
HU190628B (en)	1986-09-29	Process for preparing 3-vinyl-substituted 2,2-dimethyl-cyclopropane-1-carboxylic acids and and their esters
Brieger et al.	1968	Convenient O-alkylation of phenols
DE69016380T2 (de)	1995-08-24	Verfahren zur Herstellung von molluskiziden 2,4,5-Tribrompyrrol-3-Carbonitrilen.
IE52041B1 (en)	1987-05-27	Dioxolane derivatives for use as chemical intermediates
Hui‐Ping et al.	1996	Direct synthesis of 3‐fluoroalkyl‐2, 6‐diethoxycarbonyl phenols
US4761508A (en)	1988-08-02	1,1-(3-ethylphenyl)phenylethylene and method for preparing it
US7078571B2 (en)	2006-07-18	Preparation of 1,3-di-halo-substituted benzene derivatives
US4997989A (en)	1991-03-05	Tert-butylalkynols
Schiessler et al.	1948	Oxidation of a methylene group with hypochlorite
JP2601544B2 (ja)	1997-04-16	ジフルオロハロメトキシフェニル誘導体の製造法
CA1269994A (en)	1990-06-05	Method for producing cyclopropanecarboxylic acid derivatives
JPH05286882A (ja)	1993-11-02	２，３−ジフルオロフェノール類の製造方法
DE1618706A1 (de)	1971-04-01	Trifluormethyl-dibenzocyclohepten-5-one und Verfahren zu deren Herstellung
JP2885537B2 (ja)	1999-04-26	トラン誘導体の製造法
TW446699B (en)	2001-07-21	Process for the preparation of essentially isomerically pure methyl E-2[2-aryloxymethylenephenyl]crotonates and methyl 2-[2-aryloxymethylenephenyl]-Α-hydroxybutyrate
EP0934241B1 (en)	2001-03-14	Production of 6-bromo-2-methoxynaphthalene and derivatives