81168-90-3Relevant articles and documents
Alkynyl halide compounds and alkenyl acetate compounds therefrom
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, (2008/06/13)
The invention provides a novel method for the synthetic preparation of an ω-haloalkyne compound of the general formula R--C C--CH2)n X, in which X is a halogen atom, R is a monovalent hydrocarbon group and n is 4, 5 or 6, by the coupling reaction of a Grignard reagent RMgX' and an ω-halo-1-bromoalkyne compound of the formula X--CH2)n C C-Br. The ω-haloalkyne compound obtained in the above can be readily converted to the corresponding alkenyl acetate of the formula R--CH=CH--CH2)n OCOCH3 by first acetylating and then partially hydrogenating in the presence of a Lindlar catalyst. In particular, 7, 11-hexadecadienyl acetate, which is a sexual pheromone compound of a noxious insect, is obtained in the same route of synthesis starting with the Grignard reagent of a 1-halo-3-octene and 1, 8-dibromo-1-octyne.