A SYNTHESIS OF PURE METHYL 9-0XODECANOATE, AN INTERMEDIATE IN THE SYNTHESIS OF QUEEN HONEYBEE ESTER

publication date: Oct 2, 2012
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Journal of Apicultural Research
Vol. 22 (1) pp.22-26
DOI
          ___
Date
March 1983
Article Title
A SYNTHESIS OF PURE METHYL 9-0XODECANOATE, AN INTERMEDIATE IN THE SYNTHESIS OF QUEEN HONEYBEE ESTER
Author(s)
G. DE BROU AND A. H. REES
Abstract

Commercial methyl hydrogen nonandioate is of unsatisfactory quality for the preparation of queen honeybee methyl ester, methyl 9-oxodec-2-enoate. We give practical details for the synthesis from commercial nonandioic acid of half ester-acid chloride of high quality; this is converted to methyl 9-oxodecanoate using methyl aluminium dichloride. Queen bee ester was prepared from the ester enolate of methyl 9-oxodecanoate via methyl 9-oxo-2-phenylselenodecanoate. Details are given for careful purification at crucial stages, and the mass spectra and other spectra of a number of pure compounds are recorded.

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