GB1004959A - Process for the production of cis, trans-conjugated dienes - Google Patents

Process for the production of cis, trans-conjugated dienes

Info

Publication number
GB1004959A
GB1004959A GB5260/64A GB526064A GB1004959A GB 1004959 A GB1004959 A GB 1004959A GB 5260/64 A GB5260/64 A GB 5260/64A GB 526064 A GB526064 A GB 526064A GB 1004959 A GB1004959 A GB 1004959A
Authority
GB
United Kingdom
Prior art keywords
trans
cis
oic acid
diene
prepared
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
GB5260/64A
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.)
Bayer AG
Original Assignee
Bayer 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 Bayer AG filed Critical Bayer AG
Publication of GB1004959A publication Critical patent/GB1004959A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/09—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid esters or lactones
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Cis, trans-conjugated dienes of general formula <FORM:1004959/C2/1> where R represents -COO-alkyl, -COOH, -CH2OH or -CH2O Acyl, m is 0 to 12, and n 4 to 12, and m + n 4-16 are prepared by reacting a triaryl phosphonium halide, [Ar3P-CH2-(CH2)n-R1]+X-where Ar is a phenyl radical, R1 is -COO Alkyl or -CH2O Acyl, and X is Cl, Br or I with a proton acceptor to produce a phosphorane Ar3P = CH-(CH2)n-R1 and reacting with an aldehyde <FORM:1004959/C2/2> If R1 represents -COO Alkyl the acid R1= -COOH is prepared by alkaline hydrolysis, and the alcohol -CH2OH, is then prepared by reduction with a complex metal hydride, e.g. lithium aluminium hydride, or alternatively by direct reduction or alkaline hydrolysis of the compounds when R1 is -COO Alkyl, and -CH2OAcyl respectively. The reaction takes place at a temperature of between - 10 DEG C. and 40 DEG C., preferably in an anhydrous solvent, with an alkali metal or alkaline earth metal alkoxide or amide as proton acceptor. The products are purified by fractional distillation and the trans-trans dienes separated from the product by fractional crystallization, or in the form of urea or thiourea addition compounds. Examples describe the preparation of 10-cis, 12-trans hexadecadiene-1-oic acid, alcohol, and methyl ester, 11-cis, 13-trans-heptadecadiene-1-oic acid, alcohol and methyl ester, pentadeca-11,13-diene-1-oic acid methyl ester, 10-cis, 12-trans-tetradecadiene-1-ol, 10 - cis, 12 - trans - octadecadien-1-ol, and octadeca - 10,12 - diene - 1 - oic acid methyl ester, 9 - cis,11 - trans - pentadecadien - 1 - ol and pentadeca - 9,11 - diene - 1 - oic acid ethyl ester. The cis,trans-diene products are used as insect attractants and exhibit an anticatabolic activity. The triaryl phosphonium halides of general formula [ArP = CH-(CH2)n-R1](+)X(-), are prepared by reacting a triaryl phosphine with the halogen compounds X-CH2-(CH2)n -CH2O acyl and X-CH2-(CH2)n-CH2-COO alkyl at an elevated temperature in the presence of a solvent such as benzene, toluene, xylene, or dimethylformamide, and examples describe the preparation of [9-carbomethoxynonyl]-triphenyl phosphonium iodide, [10-carbomethoxy - decyl] - triphenyl phosphonium iodide, and [10 - acetoxy - decyl - triphenyl phosphonium bromide.
GB5260/64A 1963-02-08 1964-02-07 Process for the production of cis, trans-conjugated dienes Expired GB1004959A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEF0038958 1963-02-08

Publications (1)

Publication Number Publication Date
GB1004959A true GB1004959A (en) 1965-09-22

Family

ID=7097563

Family Applications (1)

Application Number Title Priority Date Filing Date
GB5260/64A Expired GB1004959A (en) 1963-02-08 1964-02-07 Process for the production of cis, trans-conjugated dienes

Country Status (3)

Country Link
AT (1) AT245551B (en)
GB (1) GB1004959A (en)
NL (1) NL6401031A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005087017A2 (en) 2004-03-10 2005-09-22 Natural Asa Compositions comprising reverse isomers of conjugated linoleic acid

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3485868A (en) * 1966-12-29 1969-12-23 Us Agriculture Attractants for yellow jackets (vespula spp.:vespidae)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005087017A2 (en) 2004-03-10 2005-09-22 Natural Asa Compositions comprising reverse isomers of conjugated linoleic acid
WO2005087017A3 (en) * 2004-03-10 2006-05-04 Natural Asa Compositions comprising reverse isomers of conjugated linoleic acid

Also Published As

Publication number Publication date
NL6401031A (en) 1964-08-10
AT245551B (en) 1966-03-10

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