Industrial synthesis method of dichocrocis punctiferalis sex pheromone

A synthesis method and pheromone technology, applied in the direction of organic chemistry methods, chemical instruments and methods, introduction of halogen preparation, etc., can solve the problems of harsh reaction conditions, inflammable and explosive, unsuitable for large-scale production, etc., to avoid easy Inflammable and explosive safety hazards, the effect of mild conditions

Active Publication Date: 2020-06-09
CHANGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, this kind of metal-organic compound is very active, flammable and explosive, and the reaction conditions are harsh, so it is not suitable for large-scale production

Method used

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  • Industrial synthesis method of dichocrocis punctiferalis sex pheromone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Synthesis of 10-Bromo-1-Decanol

[0025] Add 1,10-decanediol (321g, 1.712mol), toluene (1000ml), 48% hydrobromic acid (231ml, 2.054mol, 1.2eq) into a 2L three-necked flask, heat to 110°C, and reflux for 24 hours Add 48% hydrobromic acid (84ml, 0.753mol, 0.44eq) and continue heating to reflux for 24 hours. A small amount of raw material remains as detected by gas chromatography. Cool to room temperature and dilute with 500ml petroleum ether, separate the hydrobromic acid, wash the organic phase with saturated sodium bicarbonate (400ml×2) and saturated brine (400ml×2) successively, and dry over anhydrous sodium sulfate. Spin-dried and passed through the column to obtain 10-bromo-1-decanol (yield 84%).

Embodiment 2

[0027] Synthesis of 10-Hydroxydecyltriphenylphosphine Salt

[0028] Add 10-bromo-1-decanol (357g, 1.424mol), acetonitrile (1000ml), triphenylphosphine (409g, 1.566mol, 1.1eq) into a 2L three-necked flask, heat to 94°C and reflux for 48 hours. After the reaction, cool to room temperature and spin dry acetonitrile. Add 500ml of toluene, heat to reflux until homogeneous and stir for 15min, cool to room temperature, pour out the upper layer of toluene, repeat twice. Washing with diethyl ether can give white solid 10-hydroxydecyltriphenylphosphine salt with a yield of 88%.

Embodiment 3

[0030] Synthesis of 10-Hexadecen-1-ol

[0031] Add embodiment 2 gained quaternary phosphonium salt (655g, 1.278mol) in the there-necked flask of 3L mechanical stirring, tetrahydrofuran 1000ml, N 2 Open up, add potassium tert-butoxide (315g, 2.812mol, 2.2eq) in 3-4 times, control the reaction temperature below 20°C, and stir at room temperature for half an hour after the addition. Cool in an ice bath to 0°C, add a solution of n-hexanal (213g, 2.136mol, 1.2eq) in tetrahydrofuran (200ml), control the internal temperature not to exceed 5°C, after the addition is complete, react at 0°C for half an hour, then stir at room temperature for 1 hour. Add saturated ammonium chloride (500ml) to quench, separate the organic phase, extract the aqueous phase with ethyl acetate (500ml×2), wash the organic phase with brine (500ml×2), and dry over anhydrous sodium sulfate. The crude product was separated and purified by column chromatography (eluent petroleum ether / ethyl acetate=15:1~10:1) to o...

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Abstract

The invention belongs to the field of chemical synthesis, and particularly relates to an industrial synthesis method of a dichocrocis punctiferalis sex pheromone. The method comprises the following steps: taking 1, 10-decanediol as a raw material; carrying out a single-side bromination reaction to prepare 10-bromodecanol; then reacting the 10-bromodecanol with triphenylphosphine to obtain 10-hydroxydecyltriphenylphosphine salt; performing a Wittig reaction with n-hexaldehyde under the action of alkali to obtain cis-based 10-hexadecene-1-ol; performing isomerization on the cis-based enol underthe action of p-methylthiophenol to obtain trans-based 10-hexadecene-1-ol; and finally performing oxidation under the action of an oxidant to obtain the final product 10-hexadecenal. The method is mild in reaction condition and suitable for large-scale production.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, and in particular relates to an industrial synthesis method of sex pheromone of peach borer moth. Background technique [0002] Peach borer belongs to the family Lepidoptera. Alias ​​peach borer, peach borer, peach borer, leopard borer and so on. The peach borer has a mixed diet and a wide range of hosts, which can harm a variety of fruit trees and crops, such as peaches, plums, apricots, apples, pears, chestnuts, pomegranates, and sunflower discs. Peach borer larvae not only eat fruit and affect fruit development, but also excrete feces in fruit, seriously affecting fruit yield, quality and commodity value, and causing serious economic losses to fruit farmers. In recent years, with the adjustment of the agricultural industry structure, the peach tree planting area has been expanding, and the occurrence of peach borer has become increasingly serious. At present, the control of peach moth is s...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C45/29C07C47/21
CPCC07C29/62C07C29/00C07C45/29C07B2200/09C07C31/36C07C33/025C07C47/21
Inventor 陈珂杨晋夏蕾柴作笙晏羽张晨何佳怡陈新
Owner CHANGZHOU UNIV
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