Preparation of 9-alkenyl ester compounds

Details Preparation of 9-alkenyl ester compounds Preparation of 9-alkenyl ester compounds

C - Chemistry, Metallurgy

07

C

260/614, 260/432

C07C 69/145 (2006.01) C07C 6/06 (2006.01) C07C 33/025 (2006.01) C07F 3/02 (2006.01) C07F 5/00 (2006.01) C07F 5/06 (2006.01)

Patent

CA 1274246

ABSTRACT OF THE DISCLOSURE Process for the production of 9-alkenyl acetates is provided. The process comprises first disproportionating cyclo- octene with an .alpha.-olefin to give a 1,9-alkadiene. The alkadiene is metallated to form a 1-metallo-9-alkene, which is then contacted with oxygen to produce a 9-alkenyl-1-oxymetallo compound, which is optionally hydrolyzed to the corresponding alcohol, with the alco- hol being esterified to the desired 9-alkenyl ester or the 9- alkenyl-1-oxymetallo compound can be directly esterified, to pro- duce the desired 9-alkenyl esters. The esters, such as 9-dodeca- dienyl acetate, 9-tetradecenyl formate, 9-tetradecenyl acetate, 9- hexadecenyl acetate, and the like, are known pheromones or phero- mone mimics for several insect species and they are therefore useful in insect control.

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