- Method of manufacturing [...]
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PROBLEM TO BE SOLVED: To provide a method of practically producing (Z)-14-methylhexadec-8-enal in total 5 processes using inexpensive octane-1,8-diol as a starting raw material and without using pyridinium chlorochromate or hexamethylphosphoric triamide.SOLUTION: A method of producing (Z)-14-methylhexadec-8-enal includes total 5 processed including a first process of monoacetylation of octane-1,8-diol as a starting raw material, a second process of oxidation, a third process of reacting phosphonium salt having a 6-methyloctyl group with ylide generated from a base, a fourth process of carrying out alcoholysis, and a fifth process of oxidation.
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- SYNTHETIC INVESTIGATIONS INTO INSECT-ATTRACTING SUBSTANCES (SEX ATTRACTANTS). IV. SYNTHESIS OF 14-METHYL-8-cis-HEXADECENAL AND 14-METHYL-8-trans-HEXADECENAL, COMPONENTS OF THE SEX PHEROMONE OF THE DERMESTID BEETLE Trogoderma granarium EVERTS
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14-Methyl-8-hexadecyn-1-ol was obtained by the alkylation of 7-methyl-1-nonyne with heptamethylene chlorohydrin.Its hydrogenation in the presence of colloidal nickel catalyst was used for the synthesis of 14-methyl-8-cis-hexadecen-1-ol, and reduction with lithium aluminum hydride was used for the synthesis of 14-methyl-8-trans-hexadecen-1-ol.Both ethylenic alcohols were converted by oxidation into the corresponding aldehydes, which are the main components of the sex pheromone of the dermestid beetle.
- Kovalev, B. G.,Rastegaeva, V. M.
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