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Preparation method of 12-tetradecadienyl acetate of corn borer sex pheromone

A technology of tetradecenol acetate and corn borer, which is applied in the preparation of carboxylic acid esters, the preparation of organic compounds, chemical instruments and methods, etc., can solve the problems of harsh reaction conditions and low reaction selectivity, and achieves Fewer side reactions, simple and reasonable steps, and the only effect of the product

Inactive Publication Date: 2013-09-11
INST OF MICROBIOLOGY HEILONGJIANG ACADEMY OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] The above method has problems such as harsh reaction conditions, low reaction selectivity, and reactant being a Z / E body mixture.

Method used

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  • Preparation method of 12-tetradecadienyl acetate of corn borer sex pheromone
  • Preparation method of 12-tetradecadienyl acetate of corn borer sex pheromone
  • Preparation method of 12-tetradecadienyl acetate of corn borer sex pheromone

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specific Embodiment approach 1

[0033] Specific embodiment 1: Z-12-tetradecenyl acetate in the corn borer sex pheromone is based on cis-4-hexen-1-ol and 1,8-octanediol as starting materials The raw material 1,8-octanediol is unilaterally brominated to obtain 8-bromo-1-octanol, and then protected by 3,4-dihydropyran to obtain 8-bromo-1-octanol tetrahydropyran, Then react with magnesium to get 8-magnesium bromide-1-octanol tetrahydropyran; the raw material cis-4-hexene-1-alcohol reacts with p-toluenesulfonic acid chloride to get cis-4-hexene-1-p Grignard coupling reaction of benzenesulfonate, cis-4-hexene-1-p-toluenesulfonate and 8-magnesium bromide-1-octanol tetrahydropyran to obtain Z-12-tetradecene tetrahydro Pyran, then through deprotection, esterification to obtain the Z-12-tetradecenol acetate in the sex pheromone of Ostrinia sativa; the specific operation is as follows:

[0034] The first step: the preparation method of 8-bromo-1-octanol is: add 0.1mol (14.6g) 1,8-octanediol, 300mL of benzene and 0.1m...

specific Embodiment approach 2

[0040] Specific embodiment two: E-12-tetradecenyl acetate in the corn borer sex pheromone is based on crotyl alcohol and 1,10-decanediol as starting materials, wherein the raw material 1,10-decenyl Diol is unilaterally brominated to obtain 10-bromo-1-decyl alcohol, then protected by 2,3-dihydropyran to obtain 10-bromo-1-octanol tetrahydropyran, and then reacted with magnesium to obtain 10 -magnesium bromide-1-octanol tetrahydropyran; raw material crotyl alcohol reacts with p-toluenesulfonic acid chloride to obtain crotyl alcohol p-benzenesulfonate, crotyl alcohol p-benzenesulfonate and 10-magnesium bromide-1 -Octanol tetrahydropyran and E-12-tetradecene tetrahydropyran after Grignard coupling reaction, and then deprotection and esterification of the E-12-tetrahydropyran in the sex pheromone of the Asian corn borer Carbenol acetate; Specifically, carry out according to the following steps:

[0041] Step 1, the preparation method of described 10-bromo-1-decyl alcohol is as foll...

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Abstract

The invention belongs to the field of corn borer sex pheromone, and discloses a preparation method of 12-tetradecadienyl acetate of the corn borer sex pheromone. Raw materials of the method are cheap and easily available. A stereochemical structure of a Grignard reagent which is used in the method enables that the stereoisomerism of a double bond is not encountered in reaction processes, product is single, operation is convenient and safe, raw material utilization ratio is high, synthetic route is simple and reasonable, and two main components of cis(trans)-12-tetradecadienyl acetate are synthesized. Cis-4-hexen-1-ol and 1,8-octanediol are taken as the initial raw materials of Z-12-tetradecadienyl acetate; the Grignard reagent is produced from 1,8-octanediol; cis-4-hexen-1-ol reacts with 4-toluene sulfonyl chloride and then the product and 8-magnesium bromide-1-octanol tetrahydropyran are subjected to Grignard coupling reaction; the product is subjected to deprotection and esterification; and then Z-12-tetradecadienyl acetate is obtained. E-12-tetradecadienyl acetate is obtained by subjecting crotonyl alcohol and 1, 10-decanediol to the reaction processes listed above. The 12-fourteen carbon enol acetate of the invention is used as sex pheromone for corn borer control.

Description

technical field [0001] The invention belongs to the field of corn borer sex pheromone; specifically discloses the synthesis of cis-12-tetradecenyl acetate in corn borer sex pheromone and trans-12-tetradecenol acetic acid in corn borer sex pheromone ester method. Background technique [0002] The Asian corn borer (Ostrinia fumacalis Guenee) is a major pest that harms corn, sorghum and other crops, and is widely distributed in my country. Generally, the maize production can be reduced by 10% in the year of occurrence, and the reduction of maize production in the year of severe occurrence can even exceed 30%. The corn borer damages the stalk with its larvae, which is relatively hidden, difficult to be killed by pesticides, and very difficult to control. For a long time, the control of corn borer has mainly relied on chemical pesticides, but due to some habits of corn borer itself, such as complex feeding habits, larvae eating hazards, long moth moth development period, etc., ...

Claims

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Application Information

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IPC IPC(8): C07C69/145C07C67/08
Inventor 梁霆孙宇峰周舒扬
Owner INST OF MICROBIOLOGY HEILONGJIANG ACADEMY OF SCI
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