METHYL ESTER WHICH IS SYNTHETIC INTERMEDIATE FOR NEW SEX PHEROMONE OF ANOMALA RUFOCUPREA, ITS PRODUCTION AND PRODUCTION OF SEX PHEROMONE OF ANOMALA RUFOCUPREA USING THE SAME ESTER

摘要

PURPOSE:To readily obtain methyl 5-tetradencenoate which is a sex pheromone of Anomala rufocuprea in high yield by using a new methyl 5- tetramethyldecynoate as an intermediate. CONSTITUTION:1-Decyne expressed by formula I is converted into a metallic acetylide expressed by formula II (M is metallic atom, preferably Li), which is then reacted with 4-bromobutryic acid expressed by formula III to provide 5-tetradecynoic acid expressed by formula IV. The carboxylic group thereof is subsequently converted into methyl ester to afford a new substance expressed by formula V, which is then reduced with a reduction catalyst, preferably a palladium catalyst supported on one or more carriers selected from barium sulfate, barium carbonate and/or calcium carbonate and/or a palladium catalyst in which palladium supported on the calcium carbonate is poisoned with lead to readily provide the objective compound expressed by formula VI which is a sex pheromone of Anomala refocuprea in high yield.