GB1457337A - Process for preparing cis-olefinic compounds - Google Patents

Process for preparing cis-olefinic compounds

Info

Publication number
GB1457337A
GB1457337A GB4778774A GB4778774A GB1457337A GB 1457337 A GB1457337 A GB 1457337A GB 4778774 A GB4778774 A GB 4778774A GB 4778774 A GB4778774 A GB 4778774A GB 1457337 A GB1457337 A GB 1457337A
Authority
GB
United Kingdom
Prior art keywords
cis
group
olefinic compounds
tridecenol
tetradecenol
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
GB4778774A
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.)
Hoechst AG
Original Assignee
Hoechst AG
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 Hoechst AG filed Critical Hoechst AG
Publication of GB1457337A publication Critical patent/GB1457337A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C11/00—Aliphatic unsaturated hydrocarbons
    • C07C11/02—Alkenes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
    • C07C1/32—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from compounds containing hetero-atoms other than or in addition to oxygen or halogen
    • C07C1/34—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from compounds containing hetero-atoms other than or in addition to oxygen or halogen reacting phosphines with aldehydes or ketones, e.g. Wittig reaction
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/28—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/293—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/333—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
    • C07C67/343—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/09—Geometrical isomers

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

1457337 Cis-olefinic compounds HOECHST AG 5 Nov 1974 [7 Nov 1973] 47787/74 Heading C2C [Also in Division C5] Cis-olefinic compounds of formula in which R is a straight-chain or branched alkyl group (1-15C) or alkenyl group (2-15C), and R<SP>1</SP> is a straight chain or branched alkyl group (1-20C) or alkenyl group (2-20C), each of which may be substituted in the 3-position or a more remote position relative to an olefine group by a hydroxy or lower carbalkoxy group or an acyloxy group (1-3C), are prepared by dissolving an alkali metal or alkaline earth metal in a hexaalkylphosphoric triamide, adding a phosphonium salt R-CH 2 -P<SP>(+)</SP>(C 6 H 5 ) 3 Br<SP>(-)</SP>, adding an aldehyde and isolating the product. The aldehyde may be prepared in situ by addition of oxygen to the ylide solution. Examples describe the preparation of cis-9- dodecenol-, tridecenol- and tetradecenol- 1 - acetates; cis - 11 - tridecenol-, tetradecenol- and hexadecenol-1-acetates; cis-9-tetradeceneol - 1 - formate; cis - 9 - trans - 12 - tetradecadienol - 1 - acetate; cis - 9 - dodecenyl - 1 - propionate and cis - 9 - tetradecenyl - 1 - butyrate; and the cis-9-dodecenoic and cis-9-trans-12- tetradecadienoic acid methyl esters. The compounds have a phenomone effect on lepidoptera.
GB4778774A 1973-11-07 1974-11-05 Process for preparing cis-olefinic compounds Expired GB1457337A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE19732355534 DE2355534A1 (en) 1973-11-07 1973-11-07 METHOD FOR MANUFACTURING CISOLEFINS

Publications (1)

Publication Number Publication Date
GB1457337A true GB1457337A (en) 1976-12-01

Family

ID=5897374

Family Applications (1)

Application Number Title Priority Date Filing Date
GB4778774A Expired GB1457337A (en) 1973-11-07 1974-11-05 Process for preparing cis-olefinic compounds

Country Status (10)

Country Link
JP (1) JPS5077303A (en)
BE (1) BE821951A (en)
CA (1) CA1048532A (en)
CH (1) CH605486A5 (en)
DE (1) DE2355534A1 (en)
FR (1) FR2249860B1 (en)
GB (1) GB1457337A (en)
IL (1) IL45977A (en)
IT (1) IT1025448B (en)
NL (1) NL7414299A (en)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
HU176515B (en) * 1978-04-21 1981-03-28 Egyt Gyogyszervegyeszeti Gyar Composition for enticing male agrotis of cabbage
DE2834872A1 (en) * 1978-08-09 1980-02-21 Hoechst Ag INSECT LURE
US6838576B1 (en) 2003-10-23 2005-01-04 3M Innovative Properties Company Process for preparing functional group-containing olefinic compounds
JP2008280289A (en) * 2007-05-10 2008-11-20 Jfe Chemical Corp Method for producing unsaturated compound having 1-methyleneindane skeleton

Also Published As

Publication number Publication date
FR2249860B1 (en) 1978-02-24
IL45977A (en) 1977-12-30
DE2355534A1 (en) 1975-09-11
CA1048532A (en) 1979-02-13
JPS5077303A (en) 1975-06-24
FR2249860A1 (en) 1975-05-30
CH605486A5 (en) 1978-09-29
BE821951A (en) 1975-05-07
IL45977A0 (en) 1975-02-10
IT1025448B (en) 1978-08-10
NL7414299A (en) 1975-05-12

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Legal Events

Date Code Title Description
PS Patent sealed [section 19, patents act 1949]
PCNP Patent ceased through non-payment of renewal fee