INSECT PHEROMONES AND THEIR ANALOGS. IV. THE SYNTHESIS OF THE SEX ATTRACTANT OF THE HONEY BEE Apis mellifera

Article abstract of DOI:10.1007/BF00567296

A new and convenient method for the synthesis of 9-oxodec-2E-enoic acid (I) from the readily accessible octa-2E,7-dienyl acetate is proposed.From the latter compound by a series of transformations (oxidation of the terminal double bond to a ketone, saponification, hydrogenation, and oxidation with Corey's reagent) 7-oxooctanal is obtained, and this is condensed by the Knoevenagel reaction with malonic acid to give compound (I) with a yield of 69percent.