Method for the preparation of cis-11-hexadecen-1-yne

Details Method for the preparation of cis-11-hexadecen-1-yne Method for the preparation of cis-11-hexadecen-1-yne

1981-07-14

1983-05-17

Gantz, Delbert E.

Chemistry of hydrocarbon compounds

Unsaturated compound synthesis

Triple-bond product

585505, C07C 200

Patent

active

043841589

ABSTRACT:
The invention provides a novel synthetic method for the preparation of an alkyne-1 compound of the general formula R(CH.sub.2).sub.n C.tbd.CH, in which R is a monovalent hydrocarbon group and n is an integer of 4, 5 or 6, which compound is useful as an intermediate of various organic compounds or, in particular, of several sexual pheromone of noxious insects expected to give a promising means for the extermination of the insects. The method comprises reacting an .omega.-bromo-1-alkyne compound of the formula Br(CH.sub.2).sub.n C.tbd.CH, e.g. 8-bromo-1-octyne, with a Grignard reagent of the formula RMgX, e.g. cis-3-octenylmagnesium chloride, in tetrahydrofuran, preferably, in the presence of a catalyst which is dilithium copper tetrachloride or lithium copper dichloride.

REFERENCES:
patent: 4317905 (1982-03-01), Massardo et al.
Campbell et al., J. Am. Chem. Soc., 62, 1798 (1940).
Friedman et al., J. Am. Chem. Soc., 96, 7101 (1974).
J. March, Advanced Organic Chemistry, McGraw Hill, (1977), pp. 410-411.

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