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Synthesis method of (Z/E)-8-dodecen-1-alcohol acetate compound

A technology of alcohol acetate and dodecene, applied in the field of pesticides, can solve the problems of difficult post-processing, unfavorable large-scale production, and many impurities in the product

Inactive Publication Date: 2019-05-10
SHANDONG ACADEMY OF PESTICIDE SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, most of the existing methods have problems such as many side reactions, many impurities in the product, and difficult post-processing, which are not conducive to large-scale production.

Method used

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  • Synthesis method of (Z/E)-8-dodecen-1-alcohol acetate compound
  • Synthesis method of (Z/E)-8-dodecen-1-alcohol acetate compound
  • Synthesis method of (Z/E)-8-dodecen-1-alcohol acetate compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0061] (1) Synthesis of 8-bromooctanol

[0062] Put 7.3g (50mmol) of 1,8-octanediol and 10.0g of 40% hydrobromic acid (50mmol) into 150ml of toluene, heat and reflux for 8-20h, after the reaction is completed, neutralize, wash with water, and dry over anhydrous sodium sulfate , Distilled to obtain 9.9 g of 8-bromooctanol with a yield of 95%.

[0063] (2) Synthesis of 8-bromooctyl acetate

[0064] 10.4g (50mmol) 8-bromooctyl alcohol and 50mL pyridine, 5.3g (50mmol) acetic anhydride were reacted at room temperature for 24h. After the reaction was completed, the product was isolated and subjected to silica gel column chromatography to obtain 12.1g 8-bromooctyl alcohol acetate. rate 97.5%,

[0065] (3) Synthesis of ω-acetoxyoctyltriphenylphosphonium bromide salt

[0066] Put 12.50g (50mmol) of 8-bromooctyl acetate and 13.10g (50mmol) of triphenylphosphine into 150ml of benzene, heat and reflux for 20h, and when the reaction is complete, pour out the benzene layer and remove the...

Embodiment 2

[0070] (1) Synthesis of 8-bromooctanol

[0071] Put 7.3g (50mmol) of 1,8-octanediol and 10.0g of 40% hydrobromic acid (50mmol) into 120ml of toluene, heat and reflux for 8-20h, after the reaction is completed, neutralize, wash with water, and dry over anhydrous sodium sulfate , Distilled to obtain 9.6 g of 8-bromooctanol with a yield of 92.3%.

[0072] (2) Synthesis of 8-bromooctyl acetate

[0073] 10.4g (50mmol) 8-bromooctyl alcohol and 50mL pyridine, 5.3g (50mmol) acetic anhydride were reacted at room temperature for 20h. After the reaction was completed, the product was isolated and subjected to silica gel column chromatography to obtain 12.0g 8-bromooctyl alcohol acetate. Rate 96.0%,

[0074] (3) Synthesis of ω-acetoxyoctyltriphenylphosphonium bromide salt

[0075] Put 12.50 (50 mmol) of 8-bromooctyl acetate and 13.10 (50 mmol) of triphenylphosphine into 120 ml of benzene, heat and reflux for 15 hours, and when the reaction is complete, pour out the benzene layer and re...

Embodiment 3

[0079] (1) Synthesis of 8-bromooctanol

[0080] Put 7.3g (50mmol) of 1,8-octanediol and 10.0g of 40% hydrobromic acid (50mmol) into 120ml of toluene, heat and reflux for 8-20h, after the reaction is completed, neutralize, wash with water, dry over anhydrous sodium sulfate, After distillation, 9.8 g of 8-bromooctanol was obtained with a yield of 94.2%.

[0081] (2) Synthesis of 8-bromooctyl acetate

[0082] 10.4g (50mmol) 8-bromooctyl alcohol and 50mL pyridine, 5.3g (50mmol) acetic anhydride were reacted at room temperature for 24h. After the reaction was completed, the product was isolated and subjected to silica gel column chromatography to obtain 12.2g 8-bromooctyl alcohol acetate. rate 97.6%,

[0083] (3) Synthesis of ω-acetoxyoctyltriphenylphosphonium bromide salt

[0084] Put 12.50g (50mmol) of 8-bromooctyl acetate and 13.10g (50mmol) of triphenylphosphine into 120ml of benzene, heat and reflux for 15h, after the reaction is over, pour out the benzene layer, remove the...

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Abstract

The invention provides a synthesis method of a (Z / E)-8-dodecane-1-alcohol acetate compound. Specifically, the method includes the following steps: preparing 8-bromooctanol from 1,8-octanediol, then performing esterification reaction to obtain 8-Bromooctanol acetate, and then preparing omega-acetoxyoctanyl triphenyl phosphine bromide salt, and finally performing reaction through Scholoer-wittig toobtain (Z / E)-8-dodecene-1-alcohol acetate. The synthesis method has the advantages of high availability of raw materials, high yield and good selectivity, and is suitable for industrial production.

Description

technical field [0001] The invention relates to a method for synthesizing a sex pheromone of the pear borer moth, in particular a (Z / E)-8-dodecen-1-ol acetate compound, and belongs to the technical field of pesticides. Background technique [0002] The small pear borer, referred to as pear small, also known as the oriental borer moth, belongs to the family Lepidoptera Lepidoptera. It is distributed in the north and south fruit areas of our country, mainly harming pears and peaches, but also harming apples, hawthorns, apricots, jujubes and other fruit trees. The sex attractant trapping method has no pollution, no pollution, no harm to natural enemies and beneficial insects, and has been paid more and more attention by people. In 1969, Roelfs and others identified that the main component of the small pear borer was (Z)-8-dodecen-1-ol acetate, and later found that (E)-8-dodecen-1-ol acetate was also its one of the active ingredients. [0003] There are many reports on the sy...

Claims

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Application Information

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IPC IPC(8): C07C69/145C07C67/293
Inventor 张作山李旭坤江忠萍李金涛刘钦胜王滢秀
Owner SHANDONG ACADEMY OF PESTICIDE SCI
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