Alkynyl halide compounds and alkenyl acetate compounds therefrom

Details Alkynyl halide compounds and alkenyl acetate compounds therefrom Alkynyl halide compounds and alkenyl acetate compounds therefrom

1981-05-22

1983-07-05

Killos, Paul J.

Organic compounds -- part of the class 532-570 series

Organic compounds

Carboxylic acid esters

560237, C07C 6710

Patent

active

043919847

ABSTRACT:
The invention provides a novel method for the synthetic preparation of an .omega.-haloalkyne compound of the general formula R--C.tbd.C--CH.sub.2).sub.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 .omega.-halo-1-bromoalkyne compound of the formula X--CH.sub.2).sub.n C.tbd.C-Br. The .omega.-haloalkyne compound obtained in the above can be readily converted to the corresponding alkenyl acetate of the formula R--CH.dbd.CH--CH.sub.2).sub.n OCOCH.sub.3 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.

REFERENCES:
Roberts & Caseno, Basic Principles of Organic Chemistry, pp. 358 and 830 (1965).

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