GB2021104A - Preparation of a bicyclohexene - Google Patents

Preparation of a bicyclohexene

Info

Publication number
GB2021104A
GB2021104A GB7914919A GB7914919A GB2021104A GB 2021104 A GB2021104 A GB 2021104A GB 7914919 A GB7914919 A GB 7914919A GB 7914919 A GB7914919 A GB 7914919A GB 2021104 A GB2021104 A GB 2021104A
Authority
GB
United Kingdom
Prior art keywords
compound
bicyclohexene
preparation
acetyl
dimethyl
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
GB7914919A
Other versions
GB2021104B (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.)
Shell Internationale Research Maatschappij BV
Original Assignee
Shell Internationale Research Maatschappij BV
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 Shell Internationale Research Maatschappij BV filed Critical Shell Internationale Research Maatschappij BV
Publication of GB2021104A publication Critical patent/GB2021104A/en
Application granted granted Critical
Publication of GB2021104B publication Critical patent/GB2021104B/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/527—Unsaturated compounds containing keto groups bound to rings other than six-membered aromatic rings
    • C07C49/553—Unsaturated compounds containing keto groups bound to rings other than six-membered aromatic rings polycyclic
    • 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
    • C07C45/40—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with ozone; by ozonolysis
    • 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
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
    • C07C45/673—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by change of size of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/04—Saturated compounds containing keto groups bound to acyclic carbon atoms
    • C07C49/185—Saturated compounds containing keto groups bound to acyclic carbon atoms containing —CHO groups

Landscapes

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

Abstract

3-Acetyl-6,6-dimethyl-bicyclo [3.1.0]-2-hexene (Compound I) is prepared by contacting 2-(2-acetyl-3 -oxobutyl)-3,3-dimethyl- cyclopropanecarbaldehyde (Compound II) with a base in the presence of a solvent. Compound I is an intermediate in the manufacture of an insecticide, for example alpha-cyano-3-phenoxybenzyl 2-(2,2-dichlorovinyl)-3,3- dimethylcyclopropane-carboxylate. Compound II is preferably obtained from (+)-3-carene, a naturally occurring terpene.
GB7914919A 1978-05-02 1979-04-30 Preparation of a bicyclohexene Expired GB2021104B (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB1726878 1978-05-02

Publications (2)

Publication Number Publication Date
GB2021104A true GB2021104A (en) 1979-11-28
GB2021104B GB2021104B (en) 1982-06-30

Family

ID=10092215

Family Applications (1)

Application Number Title Priority Date Filing Date
GB7914919A Expired GB2021104B (en) 1978-05-02 1979-04-30 Preparation of a bicyclohexene

Country Status (6)

Country Link
JP (1) JPS54144351A (en)
CH (1) CH639932A5 (en)
DE (1) DE2917508A1 (en)
FR (1) FR2424896A1 (en)
GB (1) GB2021104B (en)
NL (1) NL7903344A (en)

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA1147346A (en) * 1978-03-02 1983-05-31 Pieter A. Verbrugge Preparation of a cyclopropanecarbaldehyde

Also Published As

Publication number Publication date
DE2917508A1 (en) 1979-11-08
NL7903344A (en) 1979-11-06
JPS54144351A (en) 1979-11-10
CH639932A5 (en) 1983-12-15
GB2021104B (en) 1982-06-30
FR2424896A1 (en) 1979-11-30

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Legal Events

Date Code Title Description
PCNP Patent ceased through non-payment of renewal fee