Synthesis method of cis-7-tetradecenol acetate, the main component of sex pheromone of Ulmus beetle moth

A technology of carbenol acetate and tetradecenol, which is applied in the field of synthesis of acetates, can solve problems such as low yield, high synthesis cost, and dangerous production process, and achieve high product yield and easy operation , low cost effect

Active Publication Date: 2017-04-26
SHANXI AGRI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the outstanding problem of the Wittig reaction is that n-butyllithium is used in the Wittig reaction. On the one hand, the production process is dangerous, on the other hand, the yield is low and the synthesis cost is high.

Method used

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  • Synthesis method of cis-7-tetradecenol acetate, the main component of sex pheromone of Ulmus beetle moth
  • Synthesis method of cis-7-tetradecenol acetate, the main component of sex pheromone of Ulmus beetle moth
  • Synthesis method of cis-7-tetradecenol acetate, the main component of sex pheromone of Ulmus beetle moth

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Embodiment 1

[0017] A method for synthesizing cis-7-tetradecenyl acetate, the main component of the sex pheromone of the elm beetle moth, comprises the following steps:

[0018] (1) Preparation of (7-bromoheptyl-1-)-2-tetrahydropyranyl ether In a 250 mL four-necked flask equipped with an electromagnetic stirrer, a reflux condenser, and a constant pressure dropping funnel, add 3 , 8 g of 4-dihydropyran, add 0.03 g of 37% hydrochloric acid as a catalyst under stirring, start to drop 17 g of 7-bromo-1-heptanol after 10 min, and control the rate of addition (this reaction is an exothermic reaction , when the drop rate of 7-bromo-1-heptanol is accelerated, the reaction will be accelerated and the exotherm will increase, and it must be cooled in an ice bath), keep the temperature of the reaction system at 40-60°C, react at room temperature for 2 hours after the addition, stop stirring, Change to a distillation device to evaporate unreacted 3, 4-dihydropyran. After the residual liquid was cooled...

Embodiment 2

[0024] (1) Preparation of (7-bromoheptyl-1-)-2-tetrahydropyranyl ether In a 500 mL four-neck flask equipped with an electromagnetic stirrer, a reflux condenser, and a constant pressure dropping funnel, add 3 , 20 g of 4-dihydropyran, under stirring, add 0.06 g of 37% hydrochloric acid as a catalyst, start to drop 34 g of 7-bromo-1-heptanol after 10 min, and control the rate of addition (this reaction is an exothermic reaction , when the drop rate of 7-bromo-1-heptanol is accelerated, the reaction will be accelerated and the exotherm will increase, and it must be cooled in an ice bath), keep the temperature of the reaction system at 40-60°C, react at room temperature for 2 hours after the addition, stop stirring, Change to a distillation device to evaporate unreacted 3, 4-dihydropyran. After the residual liquid was cooled, 170 g of petroleum ether was added, washed with saturated sodium bicarbonate solution and saturated brine, dried over sodium sulfate for 10-15 h, concentrate...

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Abstract

The invention discloses a method for synthesizing cis-7- tetradecenol acetate which is a main component of sex pheromone of holcocerus vicarius walker. The method includes (1), preparing (7-bromo-heptyl-1-)-2-tetrahydropyran ether; (2), preparing (7-bromo-heptyl-1-)-2-tetrahydropyran ether phosphonium; (3), preparing cis-7-tetradecenol tetrahydropyran ether; (4), preparing cis-7-tetradecenol; and (5), preparing the cis-7-tetradecenol acetate. The method for synthesizing the cis-7-tetradecenol acetate which is the main component of sex pheromone of holcocerus vicarius walker has the advantages that raw materials are easily available, the method is easy and convenient to implement, low in cost, high in product yield, free of risks and applicable to large-scale production, solvents are common solvents, technological processes are short, synthesis reaction conditions are mild, and products are easy to separate; contents of artificially synthesized sex pheromone can be enriched, basic chemical compounds can be provided for insect pest condition monitoring, mass trapping, mating disruption and the like on the holcocerus vicarius walker by the aid of the sex pheromone, and accordingly the method is obvious in ecological benefits and economical benefits.

Description

technical field [0001] The invention relates to the technical field of insect sex pheromones. Specifically, the invention relates to a synthesis method of enol, the main component of the sex pheromone of the eucalyptus moth, and its corresponding acetates. Background technique [0002] Elm beetle moth Holcocerus vicarius Walker belongs to Lepidoptera Lepidoptera family Cossidae, also known as willow dry wood beetle, willow black beetle moth, large brown wood beetle moth, mainly harms the branches and root necks of white elm with larvae, and secondly harms black locust, poplar and Willow, etc., are distributed in Northeast my country, North China, East China, Central China, Northwest China and other places. It is one of the harmful organisms in the "List of Forestry Dangerous Pests" issued by the State Forestry Administration in 2003. In the past, the harm occurred only in local areas. Due to the continuous drought and abnormal climate changes, the harm of the elm beetle moth...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C67/14C07C69/145
CPCC07C29/09C07C67/14C07D309/12C07C69/145C07C33/025
Inventor 杨美红陈旭鹏刘金龙刘红霞李帮同张金桐曹川健荆小院王世飞范丽华
Owner SHANXI AGRI UNIV
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