Preparation method of (8E, 10E)-8, 10-dodecadienol-1-alcohol

Abstract

The invention discloses a preparation method of (8E, 10E)-8, 10-dodecadienol-1-alcohol. The method comprises the steps of: reacting 6-chlorohexanol with trimethylchlorosilane in the presence of methyl tertiary butyl ether and triethylamine at 0 to 5 DEG C to obtain chloride trimethylethoxysilane; then performing the Grignard reaction on the chloride trimethylethoxysilane to obtain a Grignard agent; and reacting (2E, 4E)-2, 4-hexadiene-1-dryocrassyl acetate with the Grignard agent to obtain (8E, 10E)-8, 10-dodecadienol-1-triethoxysilane; and finally hydrolyzing the (8E, 10E)-8, 10-dodecadienol-1-triethoxysilane to obtain (8E, 10E)-8, 10-dodecadienol-1-alcohol. According to the preparation method, both the purity and the yield of hydroxy-protecting reaction product are relatively high; and the initiating success rate of the Grignard reaction is relatively high, the purity of the coupling reaction product is high.

Description

technical field

[0001] The present invention relates to a preparation method of sex pheromone, in particular to a preparation method of (8E,10E)-8,10-dodecadien-1-ol. Background technique

[0002] (8E,10E)-8,10-dodecadien-1-ol is the chemical name for the codling moth sex pheromone.

[0003] Chinese patent document CN101440020A discloses a preparation method of (8E,10E)-8,10-dodecadien-1-ol, the method has the following steps: 1. Mix chlorohexanol and trimethylchlorosilane in alkali; The reaction time is 3h~9h, the reaction temperature is 25℃~35℃, and then post-treatment is carried out to obtain chlorohexyloxytrimethylsilane; ②The post-treated chlorohexyloxytrimethylsilane obtained in step ① Methylsilane obtains Grignard reagent through Grignard reaction; ③ in Li 2 CuCl 4 In the presence of a catalyst, (2E,4E)-2,4-hexadien-1-ol acetate is coupled with the Grignard reagent obtained in step ②, and the temperature of the catalytic reaction is controlled by ice brine to -15°C...