FR2396745A1 - Procede pour preparer un 2-(4-chlorophenyl)-isovalerate d'alpha-cyano-3-phenoxybenzyle optiquement actif - Google Patents

Procede pour preparer un 2-(4-chlorophenyl)-isovalerate d'alpha-cyano-3-phenoxybenzyle optiquement actif

Info

Publication number
FR2396745A1
FR2396745A1 FR7820383A FR7820383A FR2396745A1 FR 2396745 A1 FR2396745 A1 FR 2396745A1 FR 7820383 A FR7820383 A FR 7820383A FR 7820383 A FR7820383 A FR 7820383A FR 2396745 A1 FR2396745 A1 FR 2396745A1
Authority
FR
France
Prior art keywords
isovalerate
chlorophenyl
cyano
phenoxybenzyl
alpha
Prior art date
Legal status (The legal status 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 status listed.)
Granted
Application number
FR7820383A
Other languages
English (en)
Other versions
FR2396745B1 (fr
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Sumitomo Chemical Co Ltd
Original Assignee
Sumitomo Chemical Co 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.)
Filing date
Publication date
Priority claimed from JP8183377A external-priority patent/JPS5416444A/ja
Priority claimed from JP12124277A external-priority patent/JPS5455546A/ja
Priority claimed from JP12207877A external-priority patent/JPS5455547A/ja
Application filed by Sumitomo Chemical Co Ltd filed Critical Sumitomo Chemical Co Ltd
Publication of FR2396745A1 publication Critical patent/FR2396745A1/fr
Application granted granted Critical
Publication of FR2396745B1 publication Critical patent/FR2396745B1/fr
Granted legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles

Abstract

L'invention concerne un procédé pour préparer un 2-(4-chlorophényl)-isovalérate d'alpha-cyano-3-phénoxybenzyle optiquement actif. On effectue l'isomérisation à l'atome de carbone asymétrique du fragment 3-phénoxybenzyle, et l'on obtient le (S)-2-(4-chlorophényl)-isovalérate de (S)-alpha-cyano-3-phénoybenzyle à partir du (S)-2-(4-chlorophényl)-isovalérate de (R,S)-alpha-cyano-3-phénoxybenzyle. Le produit obtenu a un large spectre d'activité insecticide et il est très peu toxique pour les mammifères.
FR7820383A 1977-07-07 1978-07-07 Procede pour preparer un 2-(4-chlorophenyl)-isovalerate d'alpha-cyano-3-phenoxybenzyle optiquement actif Granted FR2396745A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
JP8183377A JPS5416444A (en) 1977-07-07 1977-07-07 Optically active alpha-cyano-3-phenoxybenzyl 2-(4-chlorophenyl)-isovalerate and its preparation
JP12124277A JPS5455546A (en) 1977-10-07 1977-10-07 Preparation of optically active alpha-cyano-3-phenoxy-benzyl 2-(4-chlorophenyl)-isovalerate
JP12207877A JPS5455547A (en) 1977-10-11 1977-10-11 Preparation of optically active alpha-cyano-3-phenoxy-benzyl 2-(4-chlorophenyl)-isovalerate

Publications (2)

Publication Number Publication Date
FR2396745A1 true FR2396745A1 (fr) 1979-02-02
FR2396745B1 FR2396745B1 (fr) 1980-07-18

Family

ID=27303715

Family Applications (1)

Application Number Title Priority Date Filing Date
FR7820383A Granted FR2396745A1 (fr) 1977-07-07 1978-07-07 Procede pour preparer un 2-(4-chlorophenyl)-isovalerate d'alpha-cyano-3-phenoxybenzyle optiquement actif

Country Status (6)

Country Link
US (1) US4312816A (fr)
CH (1) CH635563A5 (fr)
DE (1) DE2830031A1 (fr)
FR (1) FR2396745A1 (fr)
GB (1) GB2001964B (fr)
NL (1) NL189962C (fr)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2394516A1 (fr) * 1977-06-13 1979-01-12 Shell Int Research Procede pour la transformation d'un stereoisomere d'un compose contenant un atome de carbone benzylique asymetrique en son diastereoisomere
FR2447905A1 (fr) * 1979-02-05 1980-08-29 Sumitomo Chemical Co (chloro-4 phenyl)-2 isovalerates d'a-cyano (halogeno-4 phenoxy)-3 benzyle optiquement actifs, leur procede de preparation et composition insecticide et/ou acaricide les contenant
FR2458542A1 (fr) * 1979-06-12 1981-01-02 Roussel Uclaf Procede de preparation d'alcools a-cyanes optiquement actifs
EP0036774B1 (fr) * 1980-03-24 1984-05-02 Sumitomo Chemical Company, Limited Préparation de 2-(4-phényl substitué)-isovalérates d'alpha-cyano-3-phénoxybenzyl optiquement actif à activité insecticide

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS55104253A (en) 1979-02-06 1980-08-09 Sumitomo Chem Co Ltd Stereoisomer of more active carboxylic ester, method of obtaining it, insecticide and acaricide comprising it
JPS56167654A (en) * 1980-05-28 1981-12-23 Sumitomo Chem Co Ltd Method for obtaining stereoisomeric mixture of more highly active phenylacetic ester derivative
DE3167334D1 (en) * 1980-10-20 1985-01-03 Sumitomo Chemical Co Preparation of insecticidal optically active isovalerate esters
DE3166207D1 (en) * 1980-11-25 1984-10-25 Ciba Geigy Ag Pesticide agents
JPS5793948A (en) * 1980-12-02 1982-06-11 Sumitomo Chem Co Ltd Preparation of stereoisomer mixture of higher active phenylacetic ester derivative
US4526727A (en) * 1983-01-24 1985-07-02 Shell Oil Company Process for preparation of an S-alpha-cyano S-alpha-isopropylphenylacetate
GB9127355D0 (en) * 1991-12-24 1992-02-19 Ici Plc Isomerisation process
US7560585B2 (en) * 2004-12-10 2009-07-14 Council Of Scientific & Industrial Research Process for preparing (S)- alpha-cyano-3-phenoxybenzyl-(S)-2-(4-chlorophenyl)-isovalerate
CN106278944A (zh) * 2016-08-10 2017-01-04 江苏春江润田农化有限公司 一种氰戊菊酯的生产方法

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1210495A (en) * 1966-11-15 1970-10-28 Struthers Scientific Int Corp Selective crystallization
US3721697A (en) * 1962-10-11 1973-03-20 Merck & Co Inc Resolution of dl-alpha-lower alkanoyl-amino-alpha-(benzyl)propionitriles
US3943181A (en) * 1971-02-27 1976-03-09 Haarmann & Reimer Gesellschaft Mit Beschrankter Haftung Separating optically pure d-l-isomers of menthol, neomenthol and isomenthol
US3996244A (en) * 1972-07-11 1976-12-07 Sumitomo Chemical Company, Limited Insecticidal esters of substituted furan methanol

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2388688A (en) * 1941-07-18 1945-11-13 Purdue Research Foundation Resolution of enantiomorphs
US3405159A (en) * 1964-11-17 1968-10-08 Merck & Co Inc Process for resolving racemic mixtures of optically-active enantiomorphs
GB1211589A (en) * 1968-08-06 1970-11-11 Ici Ltd Enantiomer isolation process
FR2375161A1 (fr) * 1976-04-23 1978-07-21 Roussel Uclaf Procede de transformation d'un ester d'acide chiral d'alcool secondaire a-cyane optiquement actif de structure (r) en ester d'acide chiral d'alcool secondaire a-cyane de structure (s)
GB1599876A (en) * 1977-06-13 1981-10-07 Shell Int Research Conversion of a stereoisomer into its diastereoisomer

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3721697A (en) * 1962-10-11 1973-03-20 Merck & Co Inc Resolution of dl-alpha-lower alkanoyl-amino-alpha-(benzyl)propionitriles
GB1210495A (en) * 1966-11-15 1970-10-28 Struthers Scientific Int Corp Selective crystallization
US3943181A (en) * 1971-02-27 1976-03-09 Haarmann & Reimer Gesellschaft Mit Beschrankter Haftung Separating optically pure d-l-isomers of menthol, neomenthol and isomenthol
US3996244A (en) * 1972-07-11 1976-12-07 Sumitomo Chemical Company, Limited Insecticidal esters of substituted furan methanol

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2394516A1 (fr) * 1977-06-13 1979-01-12 Shell Int Research Procede pour la transformation d'un stereoisomere d'un compose contenant un atome de carbone benzylique asymetrique en son diastereoisomere
FR2447905A1 (fr) * 1979-02-05 1980-08-29 Sumitomo Chemical Co (chloro-4 phenyl)-2 isovalerates d'a-cyano (halogeno-4 phenoxy)-3 benzyle optiquement actifs, leur procede de preparation et composition insecticide et/ou acaricide les contenant
FR2458542A1 (fr) * 1979-06-12 1981-01-02 Roussel Uclaf Procede de preparation d'alcools a-cyanes optiquement actifs
EP0021925A1 (fr) * 1979-06-12 1981-01-07 Roussel-Uclaf Procédé de préparation d'alcools alpha-cyanés optiquement actifs
EP0036774B1 (fr) * 1980-03-24 1984-05-02 Sumitomo Chemical Company, Limited Préparation de 2-(4-phényl substitué)-isovalérates d'alpha-cyano-3-phénoxybenzyl optiquement actif à activité insecticide

Also Published As

Publication number Publication date
GB2001964B (en) 1982-05-26
NL189962C (nl) 1993-09-16
NL7807368A (nl) 1979-01-09
DE2830031C2 (fr) 1990-04-12
US4312816A (en) 1982-01-26
GB2001964A (en) 1979-02-14
FR2396745B1 (fr) 1980-07-18
DE2830031A1 (de) 1979-01-25
CH635563A5 (fr) 1983-04-15
NL189962B (nl) 1993-04-16

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