30689-78-2Relevant academic research and scientific papers
SYNTHESIS OF (Z)- AND (E)-14-METHYL-8-HEXADECEN-1-OLS FROM METHYL (E)-5-METHYL-2,5-HEPTADIENOATE - THE CODIMER OF ISOPRENE AND METHYL ACRYLATE
Zakharkin, L. I.,Petrushkina, E. A.
, p. 37 - 41 (2007/10/02)
1-Bromo-5-methylheptane was obtained from methyl (E)-5-methyl-2,5-heptadienoate - the codimer of isoprene with methyl acrylate.During alkylation with the lithium alcoholate of lithio-8-nonyn-1-ol in the presence of HMPTA it forms 14-methyl-8-hexadecyn-1-ol.Hydrogenation of the latter at a palladium catalyst in the presence of quinoline gives (Z)-14-methyl-8-hexadecen-1-ol, and reduction with lithium aluminium hydride gives (E)-14-methyl-8-hexadecen-1-ol.
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
Kovalev, B. G.,Rastegaeva, V. M.
, p. 44 - 47 (2007/10/02)
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.
