Method for producing an ω-halo-2-alkynal
AssigneeShin-Etsu Chemical Co., Ltd.
InventorsMiyoshi Yamashita, Takehiko Fukumoto, Takeshi Kinsho
Life of this patent
Estimating the term…
Abstract
Provided is a method for industrially producing a conjugated Z-alken-yn-yl acetate such as Z-13-hexadecen-11-yn-yl acetate which is a sex pheromone component of a pine processionary moth, and an intermediate for the conjugated Z-alken-yn-yl acetate under mild conditions at a high yield. More specifically, provided is a method for producing a conjugated Z-alken-yn-yl acetate (5) comprising the steps of: reacting an ω-halo-2-alkynal (1) with an alkylidene triphenylphosphorane (3) through a Wittig reaction to obtain a conjugated Z-alken-yn-yl halide (4), and acetoxylating the conjugated Z-alken-yn-yl halide (4) into a conjugated Z-alken-yn-yl acetate (5).
Claims1
A method for producing an ω-halo-2-alkynal, comprising a step of hydrolyzing an ω-halo-1,1-dialkoxy-2-alkyne represented by formula (2):
- wherein R1 and R2 are the same or different and each represents a linear, branched or cyclic C1-10 hydrocarbon group, X represents a halogen atom, and it stands for an integer of from 2 to 15,
- into a ω-halo-2-alkynal represented by formula (1):
- in water and an organic solvent in the presence of a sulfonic acid selected from the group consisting of p-toluenesulfonic acid, methanesulfonic acid and benzensulfonic acid.
Dependencies are inferred from the claim text.