A SYNTHESIS OF PURE METHYL 9-0XODECANOATE, AN INTERMEDIATE IN THE SYNTHESIS OF QUEEN HONEYBEE ESTER
G. DE BROU AND A. H. REES
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.