Method for synthesis of sex pheromone compound of grapholitha molesta

The invention relates to a technology for a sex pheromone and a synthetic method of the pear worm, which is applied in the preparation of organic compounds, chemical instruments and methods, organic chemistry, etc., and can solve the problems such as difficulty in obtaining raw materials, harsh reaction conditions, and excessively long routes, so as to shorten the production time. Period, mild reaction conditions, and the effect of reducing production costs

Inactive Publication Date: 2012-11-28
昆明博鸿科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There are still many reports on the synthesis of sex pheromones of the pear borer, but most of them have disadva

Method used

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  • Method for synthesis of sex pheromone compound of grapholitha molesta
  • Method for synthesis of sex pheromone compound of grapholitha molesta

Examples

Experimental program
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Effect test

Embodiment 1

[0017] Embodiment 1 8-hydroxyl undecyl alcohol acetate ( 3 ) Preparation: 1,8-octanediol ( 2 ) (14.6 g, 0.1 mol) dissolved in 450ml petroleum ether, add a catalytic amount of 98% concentrated sulfuric acid, slowly add 50ml petroleum ether solution of glacial acetic acid (6 g, 0.1 mol) dropwise, continue to cool at 60-90℃ Stop the reaction after reflux reaction for 10 hours, add saturated sodium carbonate to neutralize to pH = 7-8, separate the toluene layer, extract the water layer with toluene 3 times, combine the organic layers, dry over anhydrous sodium sulfate and evaporate under reduced pressure After solvent, the crude product was obtained, and purified by column chromatography (eluent was sherwood oil and ethyl acetate) to obtain 8-hydroxyoctyl alcohol acetate ( 3 ) 15.4 g, yield 82%.

Embodiment 2

[0018] Embodiment 2 8-oxooctanyl acetate ( 4 ) preparation: 8-hydroxy octanol acetate ( 3 ) (15 g, 80 mmol) was dissolved in 400 ml of dry dichloromethane, cooling in an ice bath and adding pyridinium chlorochromate (25.86 g, 120 mmol) in batches under stirring, stirring at room temperature for 3 hours, adding an appropriate amount of water, separated dichloromethane, and extracted 2 times with dichloromethane, combined the organic layers, dried over anhydrous sodium sulfate and evaporated the solvent to obtain a crude product, which was purified by column chromatography (eluent was petroleum ether and ethyl acetate ) was purified to obtain 8-oxooctanyl acetate ( 4 ) 11.3 g, yield 75%, the crude product can also be directly used in the next reaction.

Embodiment 3

[0019] Embodiment 3 n-butyltriphenylphosphine bromide ( 6 ) preparation: n-bromobutane ( 5 ) (0.1 mol, 13.7 g) and triphenylphosphine (0.1 mol, 26.2 g) were heated to 90°C for 30 hours, washed twice with ether to obtain n-butyltriphenylphosphine bromide ( 6 )38 g, yield 95%.

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Abstract

The invention discloses a method for synthesis of a sex pheromone compound of grapholitha molesta. The method is characterized in that 1,8-octanediol and n-butylbromide are used as starting materials; 1,8-octanediol undergoes a monoesterification reaction to produce 8-hydroxyoctyl acetate; 8-hydroxyoctyl acetate is oxidized into 8-oxo-octyl acetate by pyridinium chlorochromate; and n-butyltriphenylphosphonium bromide produced by a reaction of n-butylbromide and triphenylphosphine is treated by organic bases and then undergoes a Wittig reaction with 8-oxo-octyl acetate to produce (Z/E)-8-dodecenyl acetate. The method provided by the invention has the advantages that raw materials are cheap and easily available; a synthesis route is simple; reaction conditions are mild; operation is convenient and safe; a yield is high; and a cost is low.

Description

technical field [0001] The invention relates to a method for synthesizing the sex pheromone (Z / E)-8-dodecenol acetate of the pear borer moth. Background technique [0002] Grapholitha molesta is a worldwide pest of fruit trees, also known as Grapholitha molesta, oriental fruit moth, referred to as Grapholitha molesta. For many years, chemical pesticides have been the main method of controlling pear borer-eating insects, and their drug resistance develops rapidly and causes serious environmental pollution. The use of pheromone trapping and mating interference to control pests has the advantages of no pollution, no pollution, high activity, strong specificity, and no harm to natural enemies. It is an effective biological control method and has become one of the important means to control this type of pest. First, it has received increasing attention and attention from people. [0003] In 1969, Roelofs W.L. identified the structure of the sex pheromone of pear borer as (Z)-8-...

Claims

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Application Information

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IPC IPC(8): C07C69/145C07C67/293
Inventor 陶云海黄飞杨婉秋
Owner 昆明博鸿科技有限公司
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