Method for the preparation of cis-nonen-6-yl chloride

Details Method for the preparation of cis-nonen-6-yl chloride Method for the preparation of cis-nonen-6-yl chloride

1981-04-10

1982-10-19

Warren, Charles F.

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

Organic compounds

Halogen containing

C07C 1726

Patent

active

043551939

ABSTRACT:
The invention provides a novel and efficient method for the synthetic preparation of cis-nonen-6-yl chloride which is a useful intermediate compound for the syntheses of, for example, cis-nonen-6-yl acetate, cis-nonen-6-ol, cis-nonen-6-al and the like as flavors as well as cis-dodecen-9-yl acetate and cis-tetradecen-11-yl acetate known as sexual pheromone compounds of several noxious insects. The inventive method comprises reacting 1-bromo-3-chloropropane with the Grignard reagent of cis-hexen-3-yl chloride which is a chlorination product of cis-hexen-3-ol known by a trivial name of leaf alcohol. The reaction is preferably carried out in tetrahydrofuran in the presence of a catalyst which may be lithium copper dichloride or dilithium copper tetrachloride at 0.degree. to 40.degree. C.

REFERENCES:
patent: 3033884 (1962-05-01), Osbond et al.

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