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Preparation method for trans, trans-2,4-hexadiene acetate

A technology of hexadienal acetate and hexadienol, which is applied to the preparation of carboxylic acid esters, the preparation of organic compounds, chemical instruments and methods, etc., can solve problems such as dangerous processes, difficult industrial production, and high costs. Achieve the effects of high reaction safety, easy industrial production, and low cost

Inactive Publication Date: 2013-08-21
SHANDONG ACADEMY OF PESTICIDE SCI +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] In summary, the currently reported method for synthesizing trans,trans-2,4-hexadienal acetate is expensive, dangerous, and difficult to apply to industrial production

Method used

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  • Preparation method for trans, trans-2,4-hexadiene acetate
  • Preparation method for trans, trans-2,4-hexadiene acetate
  • Preparation method for trans, trans-2,4-hexadiene acetate

Examples

Experimental program
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Effect test

Embodiment 1

[0039] Trans, the preparation method of trans-2,4-hexadienal acetate, the steps are as follows:

[0040] ①In a 500mL three-necked flask equipped with a thermometer, mechanical stirring and a constant pressure dropping funnel, add 33.6g of sorbic acid (0.3mol), 30.3g of triethylamine (0.3mol), 340g of anhydrous THF, and protect with nitrogen. Cool in an ice bath to obtain a colorless transparent liquid. Add 32.55 g (0.3 mol) of ethyl chloroformate dropwise at 0°C, keeping the temperature below 10°C. After dripping, continue to react in ice-salt bath for 2h. Gas phase monitoring, stop the reaction after the reactants are completely consumed. Quickly filter to remove triethylamine hydrochloride insoluble matter, and the filtrate is a yellow clear liquid. The solvent THF was evaporated to dryness under reduced pressure at 45°C to obtain 54.71 g of an orange liquid with a yield of 99% and a GC normalized purity of 96%.

[0041] ②In a 1L three-necked flask equipped with a mechan...

Embodiment 2

[0049] Trans, the preparation method of trans-2,4-hexadienal acetate, the steps are as follows:

[0050] ①In a 500mL three-necked flask equipped with a thermometer, mechanical stirring and a constant pressure dropping funnel, add 44.8g of sorbic acid (0.4mol), 40.4g of triethylamine (0.4mol), 450g of anhydrous ether, and protect it under nitrogen. Cool in an ice bath to obtain a colorless transparent liquid. Add 43.40 g (0.4 mol) of ethyl chloroformate dropwise at 0°C, keeping the temperature below 10°C. After dripping, continue to react in ice-salt bath for 3h. Gas phase monitoring, stop the reaction after the reactants are completely consumed. Quickly filter to remove triethylamine hydrochloride insoluble matter, and the filtrate is a yellow clear liquid. The diethyl ether was evaporated to dryness under reduced pressure at 45°C to obtain 72.94 g of an orange liquid with a yield of 99% and a GC normalized purity of 96%.

[0051] ②In a 1L three-necked flask equipped with ...

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Abstract

The invention relates to a preparation method for trans, trans-2,4-hexadiene acetate. The preparation method comprises the following steps of: reacting sorbic acid with ethyl chloroformate in a solvent under an alkaline condition to obtain sorbic acid mixed anhydride; performing reduction reaction on the sorbic acid mixed anhydride and sodium borohydride to obtain trans, trans-2,4-hexadienol; and performing acetylation reaction on the trans, trans-2,4-hexadienol and acetic anhydride to obtain the trans, trans-2,4-hexadiene acetate. According to the preparation method, cheap sorbic acid is used as a raw material, so that market supply is adequate and the cost is low; and the trans, trans-2,4-hexadienol is obtained by reduction of sodium borohydride, so that the reaction safety is high, and industrialized production is easy to perform.

Description

technical field [0001] The invention relates to a method for preparing a sex pheromone-trans, trans-2,4-hexadienal acetate, a key intermediate of the codling moth sex pheromone, and belongs to the technical field of pesticide synthesis. Background technique [0002] The codling moth Cydia pomonella (L.) is native to Europe and is a world-renowned important invasive pest that seriously endangers apple production and is an important foreign quarantine object in my country. This insect seriously harms apples, pears, sand fruits, apricots, peaches, etc., and often causes devastating damage. Even if a large amount of chemical agents are used for control, the yield will be lost by more than 20-30%, and it will cause pesticide residue pollution and affect fruit quality. and human health. The codling moth invaded Xinjiang, my country in the 1950s, and was introduced into the Hexi Corridor of Gansu Province in the 1980s, and then the spread speed gradually accelerated. From 2006 to ...

Claims

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Application Information

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IPC IPC(8): C07C69/145C07C67/08C07C33/02C07C29/147
CPCY02P20/55
Inventor 李德军江忠萍张作山陈强丁白瑜李旭坤
Owner SHANDONG ACADEMY OF PESTICIDE SCI
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