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

A technology of dodecadiene and 10-, applied in the field of -8, can solve the problems of difficult industrial production, high price, environmental, human body hazards, etc., and achieves the effects of easy procurement, low price, and cost reduction

Inactive Publication Date: 2009-05-27
JIANGSU INST OF ECOMONES +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] However, on the one hand, dihydropyran is relatively lacking in the market and is expensive, resulting in high production costs.
On the other hand, dihydropyran also has stench, is easy to cause cancer, and has great harm to the environment and human body.
Therefore, it is difficult to be suitable for industrial production

Method used

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

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Experimental program
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Embodiment 1

[0021] The preparation method of (8E, 10E)-8,10-dodecadien-1-ol of the present embodiment has the following steps:

[0022] ① A thermometer, a stirrer, a drier and a dropping funnel are installed on a 500mL reaction flask, and 100g of Cl(CH 2 ) 6 OH (0.73mol) and 78g of Na 2 CO 3 (0.74mol), the pH value of the solution is 9, slowly add 103g of (CH 3 ) 3 SiCl (0.95mol), react at 30°C for 6h after addition. Then add 200ml of water for hydrolysis; extract three times with ether, combine the ether extract, then wash the ether extract with saline and distilled water until neutral, and use CP grade anhydrous Na 2 SO 4 Dry, remove the ether solvent with normal pressure distillation, then collect (130~132) ℃ / 5mmHg cuts with vacuum distillation to obtain 139.7g of chlorohexyloxytrimethylsilane with a purity of 96%, yield up to 92%.

[0023] ②Put 10g of magnesium chips (0.416mol), 0.05g of iodine grains, and 100mL of tetrahydrofuran into a 500mL four-necked bottle, install a sti...

Embodiment 2～ Embodiment 5

[0027] The preparation method of each embodiment is basically the same as that of Example 1, and the differences are shown in Table 1.

[0028] Table 1

[0029]

[0030] In Table 1: raw material A is (2E,4E)-2,4-hexadien-1-ol acetate. Product A is chlorohexyloxytrimethylsilane. Product B is (8E,10E)-8,10-dodecadien-1-oxytrimethylsilane. Product C is (8E,10E)-8,10-dodecadien-1-ol.

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Abstract

The invention discloses a method for preparing (8E, 10E)-8, 10-dodecyl diene-1-alcohol. The method comprises the following steps: chlorine hexanol and trimethyl chlorosilane are reacted under alkaline conditions to form chlorine hexyloxy trimethyl silicane which is subjected to Grignard reaction to obtain Grignard reagent, (2E, 4E)-2, 4-hexadiene-1-alcohol acetic ester and the Grignard reagent are subjected to coupling reaction in the presence of an Li2CuCl4 catalyst to from (8E, 10E)-8, 10-dodecyl diene-1-O-trimethyl silane which is dissolved in solution of methanol and water, and paratoluenesulfonic acid is added into the solution to react to obtain the (8E, 10E)-8, 10-dodecyl diene-1-alcohol. The method uses the trimethyl chlorosilane which has advantages of low price and easy purchase in market and can lower cost as a hydroxyl protecting agent of halohydrin. The method does not produce malodor during reaction, can absorb by-products, has no pollution to environment, can not influence health of human body, and is suitable for industrialized production.

Description

technical field [0001] The 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] The chemical name of codling moth sex pheromone is (8E, 10E)-8,10-dodecadien-1-ol. In the process of artificially synthesizing codling moth sex pheromone, halogenation in the raw materials is required. The hydroxyl group of the alcohol is protected so that it has stability in subsequent reactions without destroying the structure. [0003] The most commonly used method of protecting the hydroxyl group of haloalcohols is dihydropyran As a protective agent, its reaction equation is: wherein X represents a halogen. [0004] However, on the one hand, dihydropyran is relatively scarce in the market and is expensive, resulting in high production costs. On the other hand, dihydropyran also has stench, is easy to cause cancer, and has great harm to the environment and human body. Therefore,...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C33/02C07C29/09
Inventor 孔繁蕾张锁建于斌周月根
Owner JIANGSU INST OF ECOMONES
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