CH621767A5 - Process for the preparation of optically active alkyl chrysanthemates. - Google Patents

Process for the preparation of optically active alkyl chrysanthemates. Download PDF

Info

Publication number: CH621767A5
Authority: CH; Switzerland
Prior art keywords: amino; propanol; tert; phenyl; salicylidene
Prior art date: 1975-08-01

Application number

CH977576A

Other languages

German (de)

English (en)

Inventor

Tadatoshi Aratani

Yukio Yoneyoshi

Fumio Fujita

Tsuneyuki Nagase

Original Assignee

Sumitomo Chemical Co

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.)

1975-08-01

Filing date

1976-07-30

Publication date

1981-02-27

1976-07-30 Application filed by Sumitomo Chemical Co filed Critical Sumitomo Chemical Co

1981-02-27 Publication of CH621767A5 publication Critical patent/CH621767A5/de

Links

238000000034 method Methods 0.000 title claims description 30
238000002360 preparation method Methods 0.000 title claims description 9
125000000217 alkyl group Chemical group 0.000 title description 4
-1 2-butoxyphenyl Chemical group 0.000 claims description 100
XLOPRKKSAJMMEW-SFYZADRCSA-N Chrysanthemic acid Natural products CC(C)=C[C@@H]1[C@@H](C(O)=O)C1(C)C XLOPRKKSAJMMEW-SFYZADRCSA-N 0.000 claims description 21
125000004432 carbon atom Chemical group C* 0.000 claims description 21
238000006243 chemical reaction Methods 0.000 claims description 15
239000002262 Schiff base Substances 0.000 claims description 14
150000004753 Schiff bases Chemical class 0.000 claims description 14
BXEFQPCKQSTMKA-UHFFFAOYSA-N OC(=O)C=[N+]=[N-] Chemical compound OC(=O)C=[N+]=[N-] BXEFQPCKQSTMKA-UHFFFAOYSA-N 0.000 claims description 13
150000004699 copper complex Chemical class 0.000 claims description 13
150000001414 amino alcohols Chemical class 0.000 claims description 8
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
DZPCYXCBXGQBRN-UHFFFAOYSA-N 2,5-Dimethyl-2,4-hexadiene Chemical compound CC(C)=CC=C(C)C DZPCYXCBXGQBRN-UHFFFAOYSA-N 0.000 claims description 7
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Natural products NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 6
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical class OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 claims description 6
239000004471 Glycine Substances 0.000 claims description 5
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 claims description 3
VAJVDSVGBWFCLW-UHFFFAOYSA-N 3-Phenyl-1-propanol Chemical compound OCCCC1=CC=CC=C1 VAJVDSVGBWFCLW-UHFFFAOYSA-N 0.000 claims description 3
JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical class [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 claims description 3
YGSDEFSMJLZEOE-UHFFFAOYSA-N Salicylic acid Natural products OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 claims description 3
125000000753 cycloalkyl group Chemical group 0.000 claims 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 claims description 3
239000001257 hydrogen Substances 0.000 claims description 3
229910052739 hydrogen Inorganic materials 0.000 claims description 3
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 3
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 claims description 3
229960004889 salicylic acid Drugs 0.000 claims description 3
239000002904 solvent Substances 0.000 claims description 3
NUGOTBXFVWXVTE-UHFFFAOYSA-N 2-hydroxy-3-nitrobenzaldehyde Chemical compound OC1=C(C=O)C=CC=C1[N+]([O-])=O NUGOTBXFVWXVTE-UHFFFAOYSA-N 0.000 claims description 2
KBHBGCGYQBSXRO-UHFFFAOYSA-N 2-hydroxy-6-methyl-3-propan-2-ylbenzaldehyde Chemical compound CC(C)C1=CC=C(C)C(C=O)=C1O KBHBGCGYQBSXRO-UHFFFAOYSA-N 0.000 claims description 2
125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 2
JHZOXYGFQMROFJ-UHFFFAOYSA-N 3,5-dibromo-2-hydroxybenzaldehyde Chemical compound OC1=C(Br)C=C(Br)C=C1C=O JHZOXYGFQMROFJ-UHFFFAOYSA-N 0.000 claims description 2
OFQBYHLLIJGMNP-UHFFFAOYSA-N 3-ethoxy-2-hydroxybenzaldehyde Chemical compound CCOC1=CC=CC(C=O)=C1O OFQBYHLLIJGMNP-UHFFFAOYSA-N 0.000 claims description 2
FUGKCSRLAQKUHG-UHFFFAOYSA-N 5-chloro-2-hydroxybenzaldehyde Chemical compound OC1=CC=C(Cl)C=C1C=O FUGKCSRLAQKUHG-UHFFFAOYSA-N 0.000 claims description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 2
125000003710 aryl alkyl group Chemical group 0.000 claims description 2
150000005840 aryl radicals Chemical class 0.000 claims description 2
125000005605 benzo group Chemical group 0.000 claims description 2
229910052799 carbon Inorganic materials 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims description 2
PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 claims description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
JJVNINGBHGBWJH-UHFFFAOYSA-N ortho-vanillin Chemical compound COC1=CC=CC(C=O)=C1O JJVNINGBHGBWJH-UHFFFAOYSA-N 0.000 claims description 2
125000001424 substituent group Chemical group 0.000 claims description 2
239000007795 chemical reaction product Substances 0.000 claims 2
NTCCNERMXRIPTR-UHFFFAOYSA-N 2-hydroxy-1-naphthaldehyde Chemical compound C1=CC=CC2=C(C=O)C(O)=CC=C21 NTCCNERMXRIPTR-UHFFFAOYSA-N 0.000 claims 1
SZRNTYCZUFLGEP-UHFFFAOYSA-N 3-phenyl-1-(2-propan-2-yloxyphenyl)propan-1-ol Chemical compound CC(C)OC1=CC=CC=C1C(O)CCC1=CC=CC=C1 SZRNTYCZUFLGEP-UHFFFAOYSA-N 0.000 claims 1
125000003545 alkoxy group Chemical group 0.000 claims 1
XLOPRKKSAJMMEW-UHFFFAOYSA-N chrysanthemic acid Chemical compound CC(C)=CC1C(C(O)=O)C1(C)C XLOPRKKSAJMMEW-UHFFFAOYSA-N 0.000 description 13
230000003287 optical effect Effects 0.000 description 11
239000003054 catalyst Substances 0.000 description 10
239000000203 mixture Substances 0.000 description 10
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
239000011541 reaction mixture Substances 0.000 description 7
238000003786 synthesis reaction Methods 0.000 description 7
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
239000010949 copper Substances 0.000 description 6
239000003446 ligand Substances 0.000 description 6
SDFOVBCIQOHEDY-UHFFFAOYSA-N 2-diazonio-1-(1-methyl-4-propan-2-ylcyclohexyl)oxyethenolate Chemical compound CC(C)C1CCC(C)(OC([O-])=C[N+]#N)CC1 SDFOVBCIQOHEDY-UHFFFAOYSA-N 0.000 description 5
241000723353 Chrysanthemum Species 0.000 description 5
235000007516 Chrysanthemum Nutrition 0.000 description 5
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 5
150000001879 copper Chemical class 0.000 description 5
238000004519 manufacturing process Methods 0.000 description 5
229960005335 propanol Drugs 0.000 description 5
239000000243 solution Substances 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
WDJHALXBUFZDSR-UHFFFAOYSA-M acetoacetate Chemical compound CC(=O)CC([O-])=O WDJHALXBUFZDSR-UHFFFAOYSA-M 0.000 description 4
238000009835 boiling Methods 0.000 description 4
229910052802 copper Inorganic materials 0.000 description 4
238000004817 gas chromatography Methods 0.000 description 4
239000012074 organic phase Substances 0.000 description 4
DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
238000011914 asymmetric synthesis Methods 0.000 description 3
239000002585 base Substances 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
230000007062 hydrolysis Effects 0.000 description 3
238000006460 hydrolysis reaction Methods 0.000 description 3
238000003756 stirring Methods 0.000 description 3
OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 2
KZNJGCLPCJSZEY-UHFFFAOYSA-N 2-diazo-3,4-dimethyl-3-propan-2-ylpentanoic acid Chemical compound CC(C)C(C)(C(C)C)C(=[N+]=[N-])C(O)=O KZNJGCLPCJSZEY-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
239000002253 acid Substances 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
VEMKTZHHVJILDY-UXHICEINSA-N bioresmethrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OCC1=COC(CC=2C=CC=CC=2)=C1 VEMKTZHHVJILDY-UXHICEINSA-N 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 2
125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 2
150000001993 dienes Chemical class 0.000 description 2
WASQWSOJHCZDFK-UHFFFAOYSA-N diketene Chemical compound C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
239000007789 gas Substances 0.000 description 2
238000002329 infrared spectrum Methods 0.000 description 2
230000000749 insecticidal effect Effects 0.000 description 2
OWFXIOWLTKNBAP-UHFFFAOYSA-N isoamyl nitrite Chemical compound CC(C)CCON=O OWFXIOWLTKNBAP-UHFFFAOYSA-N 0.000 description 2
230000007935 neutral effect Effects 0.000 description 2
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
239000000843 powder Substances 0.000 description 2
DSNYFFJTZPIKFZ-UHFFFAOYSA-N propoxybenzene Chemical group CCCOC1=CC=CC=C1 DSNYFFJTZPIKFZ-UHFFFAOYSA-N 0.000 description 2
239000011734 sodium Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
NDLIRBZKZSDGSO-UHFFFAOYSA-N tosyl azide Chemical compound CC1=CC=C(S(=O)(=O)[N-][N+]#N)C=C1 NDLIRBZKZSDGSO-UHFFFAOYSA-N 0.000 description 2
SJWFXCIHNDVPSH-QMMMGPOBSA-N (2S)-octan-2-ol Chemical compound CCCCCC[C@H](C)O SJWFXCIHNDVPSH-QMMMGPOBSA-N 0.000 description 1
NCJZHZJABHDELF-UHFFFAOYSA-N 1-butoxy-4-phenylbenzene Chemical group C1=CC(OCCCC)=CC=C1C1=CC=CC=C1 NCJZHZJABHDELF-UHFFFAOYSA-N 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N 1-propanol Substances CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
125000000579 2,2-diphenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(C1=C([H])C([H])=C([H])C([H])=C1[H])C([H])([H])* 0.000 description 1
PLSMHHUFDLYURK-UHFFFAOYSA-N 2,3,4-trimethyl-3-pentanol Chemical compound CC(C)C(C)(O)C(C)C PLSMHHUFDLYURK-UHFFFAOYSA-N 0.000 description 1
PVOPOJUNKWJIBJ-UHFFFAOYSA-N 2-(2-hydroxyethyliminomethyl)phenol Chemical compound OCCN=CC1=CC=CC=C1O PVOPOJUNKWJIBJ-UHFFFAOYSA-N 0.000 description 1
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
AWXVZQXIMPKRGJ-UHFFFAOYSA-N 2-diazo-3-oxobutanoic acid Chemical compound [N+](=[N-])=C(C(=O)O)C(=O)C AWXVZQXIMPKRGJ-UHFFFAOYSA-N 0.000 description 1
BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
125000004135 2-norbornyl group Chemical group [H]C1([H])C([H])([H])C2([H])C([H])([H])C1([H])C([H])([H])C2([H])* 0.000 description 1
ZNBGBHISQKMEPA-UHFFFAOYSA-N 2-oxoacetyl chloride Chemical compound ClC(=O)C=O ZNBGBHISQKMEPA-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
239000007818 Grignard reagent Substances 0.000 description 1
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 1
IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
125000003670 adamantan-2-yl group Chemical group [H]C1([H])C(C2([H])[H])([H])C([H])([H])C3([H])C([*])([H])C1([H])C([H])([H])C2([H])C3([H])[H] 0.000 description 1
238000007259 addition reaction Methods 0.000 description 1
150000001336 alkenes Chemical class 0.000 description 1
125000005907 alkyl ester group Chemical group 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
125000003118 aryl group Chemical group 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
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
150000004696 coordination complex Chemical class 0.000 description 1
229910001431 copper ion Inorganic materials 0.000 description 1
239000013078 crystal Substances 0.000 description 1
125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
150000008049 diazo compounds Chemical class 0.000 description 1
HPYNZHMRTTWQTB-UHFFFAOYSA-N dimethylpyridine Natural products CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 description 1
229910001873 dinitrogen Inorganic materials 0.000 description 1
ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 description 1
238000001035 drying Methods 0.000 description 1
ROBXZHNBBCHEIQ-BYPYZUCNSA-N ethyl (2s)-2-aminopropanoate Chemical compound CCOC(=O)[C@H](C)N ROBXZHNBBCHEIQ-BYPYZUCNSA-N 0.000 description 1
125000004494 ethyl ester group Chemical group 0.000 description 1
239000011521 glass Substances 0.000 description 1
150000004795 grignard reagents Chemical class 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
239000005457 ice water Substances 0.000 description 1
239000002917 insecticide Substances 0.000 description 1
238000011835 investigation Methods 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
239000011630 iodine Substances 0.000 description 1
239000007791 liquid phase Substances 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
YJMNLPRMBFMFDL-UHFFFAOYSA-N n-diazo-2-methylbenzenesulfonamide Chemical compound CC1=CC=CC=C1S(=O)(=O)N=[N+]=[N-] YJMNLPRMBFMFDL-UHFFFAOYSA-N 0.000 description 1
125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
ANRQGKOBLBYXFM-UHFFFAOYSA-M phenylmagnesium bromide Chemical compound Br[Mg]C1=CC=CC=C1 ANRQGKOBLBYXFM-UHFFFAOYSA-M 0.000 description 1
239000002243 precursor Substances 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
238000010992 reflux Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
230000002194 synthesizing effect Effects 0.000 description 1
125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C245/00—Compounds containing chains of at least two nitrogen atoms with at least one nitrogen-to-nitrogen multiple bond
- C07C245/12—Diazo compounds, i.e. compounds having the free valencies of >N2 groups attached to the same carbon atom
- C07C245/14—Diazo compounds, i.e. compounds having the free valencies of >N2 groups attached to the same carbon atom having diazo groups bound to acyclic carbon atoms of a carbon skeleton
- C07C245/18—Diazo compounds, i.e. compounds having the free valencies of >N2 groups attached to the same carbon atom having diazo groups bound to acyclic carbon atoms of a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
- 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
- C07F1/005—Compounds containing elements of Groups 1 or 11 of the Periodic Table without C-Metal linkages

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Catalysts (AREA)

CH977576A 1975-08-01 1976-07-30 Process for the preparation of optically active alkyl chrysanthemates. CH621767A5 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP50094349A JPS5910336B2 (ja)	1975-08-01	1975-08-01	第一菊酸エステルの不斉合成法

Publications (1)

Publication Number	Publication Date
CH621767A5 true CH621767A5 (en)	1981-02-27

Family

ID=14107796

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH977576A CH621767A5 (en)	1975-08-01	1976-07-30	Process for the preparation of optically active alkyl chrysanthemates.

Country Status (12)

Country	Link
JP (1)	JPS5910336B2 (ja)
BE (1)	BE844631A (ja)
CA (1)	CA1121813A (ja)
CH (1)	CH621767A5 (ja)
DE (1)	DE2634663C3 (ja)
DK (1)	DK142765B (ja)
FR (1)	FR2319623A1 (ja)
GB (1)	GB1499094A (ja)
IL (1)	IL50100A (ja)
IT (1)	IT1070323B (ja)
NL (1)	NL7608508A (ja)
SU (1)	SU719491A3 (ja)

Families Citing this family (14)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2919820A1 (de) *	1979-05-16	1980-11-20	Bayer Ag	Fluor-substituierte oxyalkenyl-cyclopropancarbonsaeureester, verfahren zu ihrer herstellung sowie ihre verwendung als insektizide und akarizide
EP0023075A1 (en) *	1979-07-13	1981-01-28	Imperial Chemical Industries Plc	Process for the preparation of cyclopropane carboxylic acid esters
EP0024796A1 (en) *	1979-07-13	1981-03-11	Imperial Chemical Industries Plc	Chiral amino-alcohol complexes and process for their preparation
EP0024797A1 (en)	1979-07-13	1981-03-11	Imperial Chemical Industries Plc	Chiral sugar complexes and process for their preparation
DE3064018D1 (en) *	1979-07-13	1983-08-11	Ici Plc	Process for the preparation of cyclopropane carboxylic acid esters
EP0024795A1 (en) *	1979-07-13	1981-03-11	Imperial Chemical Industries Plc	Chiral compounds and process for their preparation
JPS59158260A (ja) *	1983-02-28	1984-09-07	Seikei Giken:Kk	転写装置
JPS59158261A (ja) *	1983-07-19	1984-09-07	Seikei Giken:Kk	転写装置
JPH01232619A (ja) *	1988-03-11	1989-09-18	Toska Co Ltd	キートップの印字方法
JPH0671852A (ja) *	1992-08-31	1994-03-15	Shizuoka Giken Sanki Kk	曲面真空プレス熱転写方法及びその装置
JP4576642B2 (ja) *	1998-01-29	2010-11-10	住友化学株式会社	光学活性な菊酸の製造方法
ITMI20041211A1 (it) *	2004-06-16	2004-09-16	Endura Spa	Catalizzatori a base di complessi metallici per la sintesi di acido crisantemico otticamente attivo
CN103789789B (zh) *	2014-02-11	2016-06-29	华东师范大学	电化学合成具有光学活性的苯乙烯环状碳酸酯的方法
CN103789791B (zh) *	2014-02-12	2016-08-17	华东师范大学	一种电化学合成具有光学活性的2-苯丙酸方法

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IL44167A (en) *	1973-02-14	1979-09-30	Sumitomo Chemical Co	Chiral copper-complex catalyst

1975
- 1975-08-01 JP JP50094349A patent/JPS5910336B2/ja not_active Expired
1976
- 1976-07-22 IL IL50100A patent/IL50100A/xx unknown
- 1976-07-28 BE BE6045627A patent/BE844631A/xx not_active IP Right Cessation
- 1976-07-30 FR FR7623388A patent/FR2319623A1/fr active Granted
- 1976-07-30 CA CA000258220A patent/CA1121813A/en not_active Expired
- 1976-07-30 CH CH977576A patent/CH621767A5/de not_active IP Right Cessation
- 1976-07-30 DK DK345276AA patent/DK142765B/da not_active IP Right Cessation
- 1976-07-30 IT IT68927/76A patent/IT1070323B/it active
- 1976-07-30 NL NL7608508A patent/NL7608508A/xx not_active Application Discontinuation
- 1976-07-30 SU SU762387252A patent/SU719491A3/ru active
- 1976-07-30 GB GB31985/76A patent/GB1499094A/en not_active Expired
- 1976-08-02 DE DE2634663A patent/DE2634663C3/de not_active Expired

Also Published As

Publication number	Publication date
DE2634663B2 (de)	1979-05-31
DK345276A (ja)	1977-02-02
IL50100A0 (en)	1976-09-30
CA1121813A (en)	1982-04-13
IT1070323B (it)	1985-03-29
FR2319623B1 (ja)	1979-09-28
JPS5910336B2 (ja)	1984-03-08
DE2634663C3 (de)	1980-01-17
DE2634663A1 (de)	1977-03-17
SU719491A3 (ru)	1980-02-29
DK142765C (ja)	1981-08-17
FR2319623A1 (fr)	1977-02-25
JPS5217448A (en)	1977-02-09
GB1499094A (en)	1978-01-25
IL50100A (en)	1982-02-28
NL7608508A (nl)	1977-02-03
BE844631A (fr)	1976-11-16
DK142765B (da)	1981-01-19

Legal Events

Date	Code	Title	Description
1985-03-29	PL	Patent ceased

Publication	Publication Date	Title
CH621767A5 (en)	1981-02-27	Process for the preparation of optically active alkyl chrysanthemates.
DE2261918A1 (de)	1973-06-28	Diphenylaether und verfahren zu ihrer herstellung und verwendung
DE3737984A1 (de)	1989-08-03	3-cyano-4-phenyl-pyrrole
DE2155495A1 (de)	1973-05-10	Verfahren zur herstellung von benzylidenverbindungen
DE3928990A1 (de)	1991-03-07	Verfahren zur herstellung von (alpha)-fluoroacrylsaeurederivaten
DE3116474A1 (de)	1982-11-11	Verfahren zur herstellung von optisch aktiven carbonsaeuren
US4473709A (en)	1984-09-25	Pyrethroid intermediates and process
DE68913236T2 (de)	1994-09-29	Verfahren für die Herstellung halogenierter Sulfone.
US4197408A (en)	1980-04-08	Asymmetric synthesis of alkyl chrysanthemate
EP0008333A1 (de)	1980-03-05	Alpha-Prop-1-inyl-3-phenoxybenzylalkohole, ihre Herstellung und Verwendung als Zwischenprodukte zur Herstellung von Schädlingsbekämpfungsmitteln
DE69108195T3 (de)	1998-09-17	Astaxanthin-Zwischenprodukte.
AT203485B (de)	1959-05-25	Verfahren zur Herstellung von neuen Dinitrophenylmethacrylaten
DE3200534C2 (ja)	1992-05-14
DE1294372B (de)	1969-05-08	Verfahren zur Herstellung von Nitroacetaten bzw. Nitroketonen
EP0059687B1 (de)	1985-04-10	3-Phenoxybenzylverbindungen, Verfahren zu ihrer Herstellung und ihre Verwendung zur Synthese von bioziden Verbindungen
CH638170A5 (en)	1983-09-15	Asymmetric synthesis of chrysanthemumic acid derivatives
DE1816282A1 (de)	1969-07-17	Verfahren zur Herstellung von Hydroxy- oder Mercaptogruppen enthaltenden organischen Verbindungen
DE1955933A1 (de)	1970-11-12	Verfahren zur Herstellung von Alkoxyoctadienen
EP0151473B1 (de)	1988-01-27	Verfahren zur Herstellung von Estern optisch aktiver 2-Arylalkansäuren
DE4123585C1 (en)	1992-11-05	Fluoroolefin for insecticide and nematocide - prepd. by reacting fluoroolefin intermediate with phosphonium salt in base, for high acaricidal activity
DE68910401T2 (de)	1994-03-03	2,2-Dimethylcyclopropancarbonsäureester.
DE945759C (de)	1956-07-19	Verfahren zur Herstellung mehrfach ungesaettigter Ketone
DE3210297C2 (de)	1985-01-24	Verfahren zur Herstellung von Dichlorisonitrilcarbonsäureestern
DE2944106A1 (de)	1980-05-08	Verfahren zur herstellung von cyclo1,3,2-oxazaphosphoryl-derivaten
EP0018315A1 (de)	1980-10-29	3-(Fluorbenzyl)-benzylalkohole, Verfahren zu ihrer Herstellung, ihre Verwendung als Zwischenprodukte zur Herstellung von Insektiziden und als Ausgangsmaterialien verwendete 3-(Fluorbenzyl)-benzylaldehyde