Synthesis method of laspeyresia pomonella sex pheromone
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A synthesis method and technology of codling moth are applied in the field of synthesizing sex pheromone of codling moth, and can solve the problems of long time, high toxicity, and long route.
Inactive Publication Date: 2019-08-02
NANTONG ZHENGDA AGROCHEM
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[0006] 1. Roelofs et al. (1971) synthesized the sex pheromones E8 and E10-dodecadien-1-ol by using "Wittig reaction to construct alkenes", but the route is too long, the yield is low, and the selectivity after isomerization not good too
[0007] 2. Odinokov et al. (1985) synthesized E8, E10-dodecadien-1-ol by using 1,4,92 decatrienyltrimethylsilane as the starting material for hydroboration/oxidation of olefins, The overall yield is high, but the starting material is relatively difficult to obtain
[0009] The yield is 56%, and the stereoselectivity is better than 96%. The disadvantage is that the starting material is relatively difficult to obtain, and the quality of the intermediate product
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Embodiment 1
[0031] Intermediate A:
[0032] In a 500L dry and clean stainless steel autoclave, put 100Kg of methyl sorbate, 300Kg of methanol, and 300g of cat: 5% palladium carbon into a 500L dry and clean stainless steel autoclave, stir nitrogen replacement 3 times until there is no oxygen, heat up to 50°C, and pass in hydrogen To 6MPa, heat preservation and pressure reaction for 12h, until the reaction pressure no longer drops, cool down to 20°C, after pressure relief treatment, filter cat and activate it for reuse, concentrate the filtrate to recover methanol, and the remaining yellow oily liquid is 98.05% by GC detection . The liquid quantity is: 90.2kg, and the yield is 94.95%.
[0033] Intermediate B:
[0034] In a 500L dry and clean enamel reaction kettle, put 90.2kg of measured sorbitol, 200kg of ethyl acetate, 100kg of triethylamine, and 98kg of acetic anhydride, stir and raise the temperature to 55°C, stop the temperature rise, control 55°C, and stir the reaction After 12 hou...
Embodiment 2
[0040] Intermediate A:
[0041] In a 500L dry and clean stainless steel autoclave, put 100Kg of methyl sorbate, 200Kg of methanol, and 200g of cat: 5% palladium carbon into a 500L dry and clean stainless steel autoclave, stir nitrogen replacement 3 times until there is no oxygen, raise the temperature to 60°C, and pass in hydrogen To 5MPa, heat preservation and pressure reaction for 12h, until the reaction pressure no longer drops, cool down to 20°C, after the pressure relief treatment, filter the cat and activate it for reuse, concentrate the filtrate to recover methanol, and the remaining yellow oily liquid is 97.15% by GC detection . The amount of liquid is: 88.2kg, and the yield is 92.84%.
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Abstract
The invention relates to a synthesis method of laspeyresi pomonella sex pheromone. The method comprises the steps as follows: (1) methanol is added to methyl sorbate as a raw material, and an intermediate A sorbic alcohol is obtained through 5% palladium-carbon catalytic hydrogenation reduction; (2) the intermediate A sorbitol obtained in (1) and acetic anhydride are subjected to a reaction in ethyl acetate, triethylamine and water to obtain an intermediate B sorbic acetate; (3) 6-chlorohexanol is subjected to a reaction with trimethylchlorosilane in toluene in the presence of ethyl acetate and triethylamine, after the reaction, water is added, stirring and layering are performed, and an intermediate C6-chlorohexanol trimethylsilyl ester is obtained; (4) the intermediate B sorbic acetate and the intermediate C6-chlorohexanol trimethylsilyl ester are subjected to a reaction with sodium sand in a toluene solution, then, water and sulfuric acid are dropwise added, layering and rectification are performed, and a target product E8,E10-dodecadiene-1-ol is obtained. The synthesis method has the advantages as follows: the laspeyresi pomonella sex pheromone is synthesized from available rawmaterials, the reaction route is short, and the selectivity and product yield can be increased.
Description
technical field [0001] The invention relates to the field of chemical synthesis, in particular to a method for synthesizing codling moth sex pheromone. Background technique [0002] Insect sex pheromone is a trace chemical substance secreted by a certain sex of an insect, accepted by the receptors of the same opposite sex, and causing the opposite sex to produce a certain reproductive behavior response. In the world, the use of insect sex pheromones to monitor and control crop pests and diseases has become a feasible and widely used pest management technology. [0003] Codling moth (Laspey resia pom onella) belongs to the order Lepidoptera and belongs to the family Toricidae. It has the characteristics of wide adaptability, strong fecundity, serious damage, and difficult control. One of the serious fruit borer pests. At present, the basic control methods for pests in agricultural production mainly rely on chemical pesticides, but the long-term unrestrained use of pesticide...
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