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Method for synthesizing cis-3-tetradecanoacetate and trans-3-tetradecanoacetate

A technology of tetradecenyl acetate and tetradecenol, which is applied in the field of insect attractants, can solve the problems of high price, dangerous synthesis, and low yield of n-butyllithium, and is suitable for large-scale The production and reaction conditions are mild and the process flow is short

Inactive Publication Date: 2019-07-19
BEIJING FORESTRY UNIVERSITY
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  • Description
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  • Application Information

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Problems solved by technology

[0004] However, the outstanding problems in the Wittig reaction route are all to use n-butyllithium (this reagent is expensive, dangerous to synthesize, not easy to store, and inconvenient to use). On the one hand, there is danger in the use process, and on the other hand, the yield is low. Higher synthesis cost

Method used

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  • Method for synthesizing cis-3-tetradecanoacetate and trans-3-tetradecanoacetate
  • Method for synthesizing cis-3-tetradecanoacetate and trans-3-tetradecanoacetate
  • Method for synthesizing cis-3-tetradecanoacetate and trans-3-tetradecanoacetate

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Embodiment 1

[0034] A method for synthesizing cis-3-tetradecenyl acetate and trans-3-tetradecenyl acetate as the main components of the sex attractant of the small-horned wood beetle moth, specifically comprising the following steps:

[0035] (1) Preparation of 3-tetradecynol-1

[0036] In a 500mL four-necked round-bottom flask equipped with a stirrer, reflux condenser, and constant pressure dropping funnel, put 65mL of anhydrous tetrahydrofuran and 6.2g of magnesium chips, and slowly add 35.2g of bromine under nitrogen protection and stirring. The mixture of ethane and 24mL of tetrahydrofuran was heated slightly to initiate the reaction, then cooled to 5°C, and continued to add dropwise to dissolve the magnesium chips. After the addition, it was reacted at room temperature for 2 hours to obtain a gray suspension, and then 10.22g of Add the mixture of 3-butynol-1 and 8mL tetrahydrofuran within 40 minutes, continue to react at room temperature for 3 hours, lower the temperature to 0°C, add ...

Embodiment 2

[0046] (1) Preparation of 3-tetradecynol-1

[0047] In a 1000mL four-neck round bottom flask equipped with a stirrer, reflux condenser, and constant pressure dropping funnel, put 140mL of anhydrous tetrahydrofuran and 12.5g of magnesium chips, and slowly add 70.5g of bromine under nitrogen protection and stirring. The mixed solution of ethane and 50mL tetrahydrofuran was slightly heated to initiate the reaction, then cooled to 5°C, and continued to add dropwise to dissolve the magnesium chips. After the addition, it was reacted at room temperature for 2 hours to obtain a gray suspension, and then added dropwise with 20.5g of Add the mixture of 3-butynol-1 and 15mL tetrahydrofuran within 40 minutes, continue to react at room temperature for 3 hours, cool down to 0°C, add 0.8 g of newly prepared cuprous chloride, stir for 15 minutes, the suspension turns from gray to Yellow, then dropwise add a mixture of 40.8g of 1-bromo-decane and 30mL of tetrahydrofuran, reflux at 65-70°C for...

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Abstract

The invention discloses a method for synthesizing cis-3-tetradecanoacetate and trans-3-tetradecanoacetate. The method comprises the following steps: (1) preparing 3-tetradecyne alcohol-1; (2) preparing cis-3-tetradecenol-1; (3) preparing trans-3-tetradecenol-1; and (4) preparing the cis-3-tetradecanoacetate and trans-3-tetradecanoacetate. The method is used for synthesizing cis-3-tetradecanoacetate and trans-3-tetradecanoacetate which are main components of gyplure of holcocerus insularis Staudinger; the raw materials for reaction are easily obtained; the cost is low; technical processes are short; reaction conditions are mild; the operation is simple, convenient and free from risk; the product is easily separated; the yield is high; and massive production can be carried out.

Description

technical field [0001] The present invention relates to the technical field of insect sex attractants, in particular to a synthetic main component of the sex attractant of the small-horned wood beetle moth cis-3-tetradecenol acetate and trans-3-tetradecenol ethyl ester method. Background technique [0002] Streltzoviella insularis (Staudinger) belongs to Lepidoptera (Lepidoptera) Cossidae. It is an important dry borer pest in my country. It mainly damages ash, ginkgo, Chinese pagoda tree, elm and paper tree with its larvae. , the number of insects per plant can reach hundreds, and it has occurred in large areas in Beijing, Tianjin, Hebei, Jiangsu, Jiangxi, Hunan, Shanghai and other provinces and cities. The prevention and control brings great difficulties, leading to a significant reduction in the use value, aesthetics and protection efficiency of forest trees, which seriously threatens ecological construction and economic development. [0003] The use of insect sex attracta...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C67/14C07C69/145C07C29/17C07C33/025
CPCC07B2200/09C07C29/17C07C29/34C07C67/14C07C33/042C07C33/025C07C69/145
Inventor 宗世祥骆有庆张金桐任利利刘金龙陶静黄建东
Owner BEIJING FORESTRY UNIVERSITY
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