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GB1459285A - Process for the preparation of cyclopropane carboxylic acid esters - Google Patents

Process for the preparation of cyclopropane carboxylic acid esters

Info

Publication number
GB1459285A
GB1459285A GB5223174A GB5223174A GB1459285A GB 1459285 A GB1459285 A GB 1459285A GB 5223174 A GB5223174 A GB 5223174A GB 5223174 A GB5223174 A GB 5223174A GB 1459285 A GB1459285 A GB 1459285A
Authority
GB
United Kingdom
Prior art keywords
ester
carboxylic acid
dichlorovinyl
pentadiene
dichloro
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.)
Expired
Application number
GB5223174A
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.)
Imperial Chemical Industries Ltd
Original Assignee
Imperial Chemical Industries 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
Application filed by Imperial Chemical Industries Ltd filed Critical Imperial Chemical Industries Ltd
Priority to GB5223174A priority Critical patent/GB1459285A/en
Priority to AU87049/75A priority patent/AU491964B2/en
Priority to FR7536836A priority patent/FR2293415A1/en
Priority to JP14301975A priority patent/JPS5921857B2/en
Priority to DE19752554380 priority patent/DE2554380A1/en
Publication of GB1459285A publication Critical patent/GB1459285A/en
Expired legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Dentistry (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Agronomy & Crop Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

1459285 Cyclopropane carboxylic acid esters IMPERIAL CHEMICAL INDUSTRIES Ltd 21 Nov 1975 [3 Dec 1974] 52231/74 Heading C2C The invention comprises a process for the preparation of an ester of 3-(2,2-dichlorovinyl)- 2,2 - dimethylcyclopropane carboxylic acid which comprises the steps of (a) causing an ester of glycine in the form of a water-soluble acid addition salt to react with an alkali metal nitrite in an aqueous medium in a first vessel, said aqueous medium being in interfacial contact with a solvent having a boiling point less than the boiling point of 1,1-dichloro-4-methyl-1,3- pentadiene and which is immiscible with the said aqueous medium and into which the ester of diazoacetic acid thus formed is preferentially dissolved, (b) continuously transferring a stream of said solvent containing the ester of diazoacetic acid into a second vessel containing an excess of 1,1-dichloro-4-methyl-1,3-pentadiene held at a sufficiently high temperature that the solvent is readily distilled therefrom, there also being present a catalyst to catalyse the release of nitrogen from the initial reaction product of the reaction between the ester of diazoacetic acid and 1,1-dichloro-4-methyl-1,3-pentadiene to form the ester of 3-(2,2-dichlorovinyl)-2,2- dimethylcyclopropane carboxylic acid, and (c) removing the mixture of the diene and the ester of 3-(2,2-dichlorovinyl)-2,2-dimethyl-cyclopropane carboxylic acid from the second vessel and distilling the diene from the said mixture.
GB5223174A 1974-12-03 1974-12-03 Process for the preparation of cyclopropane carboxylic acid esters Expired GB1459285A (en)

Priority Applications (5)

Application Number Priority Date Filing Date Title
GB5223174A GB1459285A (en) 1974-12-03 1974-12-03 Process for the preparation of cyclopropane carboxylic acid esters
AU87049/75A AU491964B2 (en) 1975-11-27 A process forthe preparation of cyclopropane carboxylic acid esters
FR7536836A FR2293415A1 (en) 1974-12-03 1975-12-02 PROCESS FOR PREPARING ESTERS OF A CYCLOPROPANE-CARBOXYLIC ACID AND PRODUCTS OBTAINED
JP14301975A JPS5921857B2 (en) 1974-12-03 1975-12-03 3 (2 2-dichlorovinyl) -2 2- dimethylcyclopropane carbonate ester
DE19752554380 DE2554380A1 (en) 1974-12-03 1975-12-03 PROCESS FOR PREPARING AN ESTER FROM 3- (2,2-DICHLOROVINYL) -2,2-DIMETHYLCYCLOPROPANE CARBONIC ACID

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB5223174A GB1459285A (en) 1974-12-03 1974-12-03 Process for the preparation of cyclopropane carboxylic acid esters

Publications (1)

Publication Number Publication Date
GB1459285A true GB1459285A (en) 1976-12-22

Family

ID=10463127

Family Applications (1)

Application Number Title Priority Date Filing Date
GB5223174A Expired GB1459285A (en) 1974-12-03 1974-12-03 Process for the preparation of cyclopropane carboxylic acid esters

Country Status (4)

Country Link
JP (1) JPS5921857B2 (en)
DE (1) DE2554380A1 (en)
FR (1) FR2293415A1 (en)
GB (1) GB1459285A (en)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4343935A (en) 1979-07-13 1982-08-10 Imperial Chemical Industries Limited Chiral compounds
US4350811A (en) 1979-07-13 1982-09-21 Imperial Chemical Industries Limited Chiral sugar complexes
US4383112A (en) 1979-07-13 1983-05-10 Imperial Chemical Industries Limited Chiral amino-alcohol complexes
CN109776351A (en) * 2017-11-15 2019-05-21 江苏优士化学有限公司 A kind of continuous synthesis method of diazoacetate
CN111978181A (en) * 2020-09-25 2020-11-24 湖北中灏科技有限公司 High-yield preparation method of ethyl chrysanthemate
CN112142597A (en) * 2020-09-25 2020-12-29 湖北中灏科技有限公司 Preparation method of ethyl chrysanthemate
WO2023178814A1 (en) * 2022-03-25 2023-09-28 杭州国瑞生物科技有限公司 Method for preparing intermediate of paxlovid

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1553638A (en) * 1977-03-11 1979-09-26 Ici Ltd Preparation of cyclopropane carboxylic acid esters

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3897478A (en) * 1970-05-21 1975-07-29 Stauffer Chemical Co Continuous process for the manufacture of alkyl chrysanthemate esters

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4343935A (en) 1979-07-13 1982-08-10 Imperial Chemical Industries Limited Chiral compounds
US4350811A (en) 1979-07-13 1982-09-21 Imperial Chemical Industries Limited Chiral sugar complexes
US4383112A (en) 1979-07-13 1983-05-10 Imperial Chemical Industries Limited Chiral amino-alcohol complexes
CN109776351A (en) * 2017-11-15 2019-05-21 江苏优士化学有限公司 A kind of continuous synthesis method of diazoacetate
CN109776351B (en) * 2017-11-15 2021-11-09 江苏优士化学有限公司 Diazoacetic ester continuous synthesis method
CN111978181A (en) * 2020-09-25 2020-11-24 湖北中灏科技有限公司 High-yield preparation method of ethyl chrysanthemate
CN112142597A (en) * 2020-09-25 2020-12-29 湖北中灏科技有限公司 Preparation method of ethyl chrysanthemate
CN111978181B (en) * 2020-09-25 2022-11-15 湖北中灏科技有限公司 High-yield preparation method of ethyl chrysanthemate
CN112142597B (en) * 2020-09-25 2022-11-15 湖北中灏科技有限公司 Preparation method of ethyl chrysanthemate
WO2023178814A1 (en) * 2022-03-25 2023-09-28 杭州国瑞生物科技有限公司 Method for preparing intermediate of paxlovid

Also Published As

Publication number Publication date
FR2293415A1 (en) 1976-07-02
JPS5182244A (en) 1976-07-19
JPS5921857B2 (en) 1984-05-22
AU8704975A (en) 1977-06-02
FR2293415B1 (en) 1979-07-13
DE2554380A1 (en) 1976-06-10

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Legal Events

Date Code Title Description
PS Patent sealed
48S Specification amended (sect. 8/1949)
SP Amendment (slips) printed
PE20 Patent expired after termination of 20 years

Effective date: 19951120