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Synthesis method of cis (trans)-8-dodecenol acetate

A technology of carbenol acetate and synthesis method, which is applied in the field of artificial synthesis of insect sex pheromones, can solve the problems of high synthesis cost, difficult to obtain raw materials, cumbersome operation process, etc., achieve few steps, low production cost, and high production efficiency. The effect of simple process

Pending Publication Date: 2021-11-16
PHEROBIO TECHNOLOGY CO LTD +1
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0010] For this reason, the technical problem to be solved by the present invention is to provide a kind of synthetic method of cis (trans)-8-dodecenol acetate, to solve the difficulty of obtaining the raw materials existing in the synthesis of the sex pheromone of the current pear borer moth , cumbersome operation process and high synthesis cost

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  • Synthesis method of cis (trans)-8-dodecenol acetate
  • Synthesis method of cis (trans)-8-dodecenol acetate
  • Synthesis method of cis (trans)-8-dodecenol acetate

Examples

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Embodiment 1

[0047] A kind of synthetic method of cis (trans)-8-dodecenol acetate, comprises the steps:

[0048] (1) At room temperature, place 1,8-octanediol in acetic acid aqueous solution, use sulfuric acid as a catalyst, and stir continuously to make 1,8-octanediol and acetic acid react to generate 8-acetoxy-1-octanol ; Use a continuous centrifugal extractor to continuously extract the 8-acetoxyl-1-octanol generated by the reaction with petroleum ether, after continuous extraction for 20 hours, obtain the petroleum ether phase, distill the petroleum ether in the petroleum ether phase, wait for the petroleum ether to evaporate After drying, 8-acetoxyl-1-octanol is obtained; the rotating speed of the continuous centrifugal extractor is 1450r / min, and the steamed petroleum ether continues to enter the continuous centrifugal extractor, and the petroleum ether is recycled and used;

[0049] (2) Add water, ethyl acetate, sodium bromide and sodium acetate trihydrate to 8-acetoxy-1-octanol, st...

Embodiment 2

[0070] The present embodiment is similar to the method of embodiment 1, and the difference between the two is as follows:

[0071] In step (1), the molar ratio of 1,8-octanediol, sulfuric acid and acetic acid is 1:0.5:5; in the acetic acid aqueous solution, the mass concentration of acetic acid is 25wt%;

[0072] In step (2), the molar ratio of 8-acetoxy-1-octanol, water, ethyl acetate, sodium bromide, sodium acetate trihydrate, tetramethylpiperidine oxide and sodium hypochlorite is 1:15: 10:0.5:0.5:0.005:1;

[0073] In step (3), in the preparation method of organic base: the molar ratio of sodium hydride, tetrahydrofuran and dimethyl sulfoxide is 1:1:2; in step (3), organic base, butyl triphenyl bromide The molar ratio of phosphine and 8-acetoxy-1-octanal is 2.5:1:1.

[0074] In this example, the yield of 8-acetoxy-1-octanol prepared in step (1) was 80%, and the yield of 8-acetoxy-1-octanal prepared in step (2) was 98%. %; The yield of the cis (trans)-8-dodecenol acetate p...

Embodiment 3

[0076] The present embodiment is similar to the method of embodiment 1, and the difference between the two is as follows:

[0077] In step (1), the extraction time is 10h;

[0078] In step (2-2), the temperature of the reaction system A is lowered to 0°C, the sodium hypochlorite solution is added dropwise, and the temperature of the reaction system A is controlled between 10°C, after the sodium hypochlorite solution is added dropwise, Insulated reaction at 10°C for 1 hour to obtain reaction system B;

[0079] In step (3-1) and step (3-2), the reaction temperature is controlled at -50°C.

[0080] In this example, the yield of 8-acetoxy-1-octanol prepared in step (1) was 75%, and the yield of 8-acetoxy-1-octanal prepared in step (2) was 94%. %; the yield of the cis (trans)-8-dodecenol acetate prepared by step (3) is 75%.

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Abstract

The invention discloses a synthesis method of cis (trans)-8-dodecenol acetate. The method comprises the following steps: placing 1, 8-octylene glycol in an acetic acid aqueous solution at normal temperature, and continuously stirring to react by taking sulfuric acid as a catalyst; continuously extracting the reaction system with petroleum ether in a centrifugal extractor, and obtaining 8-acetoxy-1-octanol after petroleum ether is recovered through distillation; adding water, ethyl acetate, sodium bromide and sodium acetate trihydrate into 8-acetoxy-1-octanol, stirring, adding tetramethylpiperidine oxide, dropwise adding sodium hypochlorite, stirring while dropwise adding, and reacting to generate 8-acetoxy-1-octanal; adding butyl triphenyl phosphonium bromide into tetrahydrofuran, dropwise adding organic alkali while stirring to react, continuously dropwise adding 8-acetoxy-1-octanal, and carrying out wittig reaction to generate the cis (trans)-8-dodecenol acetate. The method has the advantages of short period, few steps, high yield, simple post-treatment and the like, and is suitable for large-scale industrial production.

Description

technical field [0001] The invention relates to the technical field of artificial synthesis of insect sex pheromones. Specifically, it is a synthetic method of cis (trans)-8-dodecenol acetate. Background technique [0002] Grapholithamolesta, also known as Grapholithamolesta, is a worldwide pest, also known as Grapholithamolesta, oriental fruit borer moth, which belongs to the family Lepidoptera. The small pear borer is widely distributed in China. Except for Tibet, it occurs commonly in North China, Central China, South China, and Northeast China. It damages pears, apples, peaches, hawthorns, apricots, cherries and other fruit trees. The larvae of the small pear borer eat fruit and young shoots, and the occurrence is relatively large in recent years, and the damage is becoming more and more serious. In general, the damage rate of pome fruit reaches about 10%, and in individual orchards it reaches 20% to 30%, and in orchards without spraying, the rate of insect fruit can r...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C69/145C07C67/28
CPCC07C67/08C07C67/28C07F9/5352C07B2200/09C07C69/16C07C69/14C07C69/145
Inventor 杨树生崔艮中徐文泉
Owner PHEROBIO TECHNOLOGY CO LTD
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