FR2421876A1 - Racemisation of ester of chiral acid - and alpha-cyano-(3)-phenoxybenzyl alcohol, includes treatment of esters with basic agent and gives insecticidal prod. - Google Patents

Racemisation of ester of chiral acid - and alpha-cyano-(3)-phenoxybenzyl alcohol, includes treatment of esters with basic agent and gives insecticidal prod.

Info

Publication number
FR2421876A1
FR2421876A1 FR7717014A FR7717014A FR2421876A1 FR 2421876 A1 FR2421876 A1 FR 2421876A1 FR 7717014 A FR7717014 A FR 7717014A FR 7717014 A FR7717014 A FR 7717014A FR 2421876 A1 FR2421876 A1 FR 2421876A1
Authority
FR
France
Prior art keywords
configuration
ester
esters
cyano
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
FR7717014A
Other languages
French (fr)
Other versions
FR2421876B1 (en
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.)
Sanofi Aventis France
Original Assignee
Roussel Uclaf 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.)
Filing date
Publication date
Priority claimed from FR7612094A external-priority patent/FR2375161A1/en
Application filed by Roussel Uclaf SA filed Critical Roussel Uclaf SA
Priority to FR7717014A priority Critical patent/FR2421876A1/en
Publication of FR2421876A1 publication Critical patent/FR2421876A1/en
Application granted granted Critical
Publication of FR2421876B1 publication Critical patent/FR2421876B1/fr
Granted legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C255/53—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and hydroxy groups bound to the carbon skeleton

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Conversion of an ester of a chiral acid (I) and an optically active alpha-cyano-3-pheroxy-benzyl alcohol (II) having R or racemic R,S configuration or of a non-equimolecular mixt. of the ester of (I) with R configuration (II) and the ester of (I) with S configuration (II) (called "ester (R+S)") to give an ester of the chiral acid (I) with (II) having S configuration. Process is characterised in that the starting esters are treated with a basic agent chosen from ammonia, prim, sec or tert. amines, quat. ammonium derivs, basic ion-exchange resins, high mol. wt. liq. amines and strong bases, which are used in catalytic amts., in a solvent (mixt.) in which the ester of (I) with S configuration (II) is insoluble and the ester for (I) with R configuration (II) is soluble and then isolating the ester of (I) with S configuration (II). Esters of alpha-cyano-3-pheroxy-benzyl alcohol having S configuration and having R configuration with 2,2-dimethyl-3R-(2,2-dichlorovinyl)- cyclopropane-IR-caroxylic acid are new. prods. are useful as Insecticides active against aphids, larvae of lepidoptera, coleoptera, flies, mosquitos etc. The esters of 2,2-dimethyl-3R-(2,2-dihalovinyl)-cyclopropene-IR-carboxylic with S configuration (II) have superior activity to those with R configuration (II).
FR7717014A 1976-04-23 1977-06-03 Racemisation of ester of chiral acid - and alpha-cyano-(3)-phenoxybenzyl alcohol, includes treatment of esters with basic agent and gives insecticidal prod. Granted FR2421876A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
FR7717014A FR2421876A1 (en) 1976-04-23 1977-06-03 Racemisation of ester of chiral acid - and alpha-cyano-(3)-phenoxybenzyl alcohol, includes treatment of esters with basic agent and gives insecticidal prod.

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR7612094A FR2375161A1 (en) 1976-04-23 1976-04-23 PROCESS FOR TRANSFORMATION OF AN OPTICALLY ACTIVE A-CYANE SECONDARY ALCOHOL CHIRAL ACID ESTER OF STRUCTURE (R) INTO A-CYANE SECONDARY ALCOHOL CHIRAL ACID ESTER OF STRUCTURE (S)
FR7717014A FR2421876A1 (en) 1976-04-23 1977-06-03 Racemisation of ester of chiral acid - and alpha-cyano-(3)-phenoxybenzyl alcohol, includes treatment of esters with basic agent and gives insecticidal prod.

Publications (2)

Publication Number Publication Date
FR2421876A1 true FR2421876A1 (en) 1979-11-02
FR2421876B1 FR2421876B1 (en) 1980-09-12

Family

ID=26219416

Family Applications (1)

Application Number Title Priority Date Filing Date
FR7717014A Granted FR2421876A1 (en) 1976-04-23 1977-06-03 Racemisation of ester of chiral acid - and alpha-cyano-(3)-phenoxybenzyl alcohol, includes treatment of esters with basic agent and gives insecticidal prod.

Country Status (1)

Country Link
FR (1) FR2421876A1 (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2471187A1 (en) * 1979-12-10 1981-06-19 Roussel Uclaf NEW COMPOSITIONS FOR THE CONTROL OF PARASITES OF HOT-BLOOD ANIMALS

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2471187A1 (en) * 1979-12-10 1981-06-19 Roussel Uclaf NEW COMPOSITIONS FOR THE CONTROL OF PARASITES OF HOT-BLOOD ANIMALS

Also Published As

Publication number Publication date
FR2421876B1 (en) 1980-09-12

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