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Synthesizing method for 5E-decene-1-alcohol and acetic acid 5E-decenoate

A synthetic method and technology of decene, applied in the preparation of carboxylic acid esters, chemical instruments and methods, and preparation of carbon-based compounds, etc., can solve problems such as high cost, difficult industrial production, and complicated steps

Active Publication Date: 2017-02-22
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

These synthetic methods are complicated in steps, high in cost, and low in yield, making it difficult for industrial production

Method used

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  • Synthesizing method for 5E-decene-1-alcohol and acetic acid 5E-decenoate

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preparation example Construction

[0033] The invention provides a kind of synthetic method of 5E-decen-1-ol, comprising the steps of:

[0034] (1) In a solution system, acrolein, lithium bromide and acetylene are subjected to a coupling reaction in the presence of a palladium catalyst to obtain 5-bromo-4E-pentenal;

[0035] (2) Under inert gas protection conditions, methoxymethyltriphenylphosphine chloride, basic substance, 5-bromo-4E-pentenal and anhydrous organic solvent are mixed for reaction to obtain 1E, 5E- 1-bromo-6-methoxyhexadiene;

[0036] (3) Under inert gas protection conditions, the catalyst, 1E, 5E-1-bromo-6-methoxyhexadiene, and n-butylmagnesium bromide are dissolved in anhydrous organic solvent and reacted to obtain 1E, 5E- 1-Methoxydecadiene;

[0037] (4) dissolving the 1E,5E-1-methoxydecadiene obtained in the step (3) in a mixed solvent of acetic acid, tetrahydrofuran and water, and undergoing a hydrolysis reaction to obtain 5E-decenal;

[0038] (5) Mix 5E-decenal, a reducing agent, sodium...

Embodiment 1

[0077] Dissolve 2.5 mol of acrolein, 3 mol of lithium bromide and 2.5 mmol of palladium acetate in a mixed solvent of acetic acid and water, pass through acetylene scrubbed with sulfuric acid, stir and react at room temperature for 48 hours, add saturated sodium carbonate solution to neutralize properties, separated the organic layer, extracted the aqueous layer with 3×200mL dichloromethane, combined the organic layers and washed with water, and then washed with anhydrous Na 2 SO 4 The organic layer was dried, and the solvent was evaporated to obtain 350 g of 5-bromo-4E-pentenal, with a yield of 86%;

[0078] Under the protection of nitrogen and in an ice bath, dissolve 1.5 mol of methoxymethyltriphenylphosphine chloride in anhydrous tetrahydrofuran, add 1.5 mol of potassium tert-butoxide in 3 times, and stir for 1 hour to obtain a red solution. -Bromo-4E-pentenal 1mol 1L anhydrous tetrahydrofuran solution was added dropwise to the reaction mixture, stirred and reacted for 12...

Embodiment 2

[0084] Dissolve 3 mol of acrolein, 3.6 mol of lithium bromide and 3 mmol of palladium chloride in trifluoroacetic acid, pass through acetylene scrubbed with sulfuric acid, stir and react at room temperature for 36 hours, add saturated sodium carbonate solution to neutralize until neutral, separate The organic layer and the aqueous layer were extracted with 3×200mL ether, the combined organic layers were washed with water, and then washed with anhydrous Na 2 SO 4 The organic layer was dried, and the solvent was evaporated to obtain 425 g of 5-bromo-4E-pentenal, with a yield of 87%;

[0085] Under the protection of nitrogen and in an ice bath, dissolve 2 mol of methoxymethyltriphenylphosphine chloride in toluene, add 2.1 mol of sodium hydride in 3 portions, stir for 1 hour to obtain a red solution, and 5-bromo-4E- 1L toluene solution of 2 mol of pentenal was added dropwise to the reaction mixture, stirred and reacted for 12 hours, 1L of water was added, the water layer was sepa...

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Abstract

The invention provides a synthesizing method for 5E-decene-1-alcohol and acetic acid 5E-decenoate. With acrylaldehyde and acetylene being raw materials, a coupling reaction is carried out under the existence of a palladium catalyst to obtain 5-bromo-4E-pentenal, 5-bromo-4E-pentenal and methoxy methyl-triphenyl phosphonium chloride are subjected to a Wittig reaction to obtain 1E,5E-1-bromo-6-methoxy hexadiene, then 1E,5E-1-bromo-6-methoxy hexadiene and butyl magnesium bromide are subjected to a Kumada coupling reaction to obtain 1E,5E-1-methoxy decadiene, 5E-decenal is obtained through hydrolysis, then 5E-decene-1-alcohol is obtained through reducing, and finally the acetic acid 5E-decenyl acetate is obtained after esterification. The raw materials used for synthesis are low in price and easy to obtain, the synthesizing route is simple, reaction conditions are mild, operation is convenient and safe, industrialized production is easy, the yield is high, and the synthesizing method has important meaning for prevention and treatment of anarsia lineatella.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a method for synthesizing sex pheromone 5E-decen-1-ol and 5E-decenyl acetate. Background technique [0002] The peach moth belongs to the genus Lepidoptera and is an important pest of peaches and apricots. The first-generation larvae mainly damage new shoots and flowers, while the next-generation larvae mainly feed on fruits. Hazards can cause significant economic losses. [0003] At present, chemical pesticides are still the basic means of pest control in agriculture, but the long-term use of pesticides in large quantities has caused many side effects, the use of pesticides has increased due to the resistance of pests, the cost of control has increased, and control has become increasingly difficult, destroying ecological balance, killing a large number of natural enemies, and polluting Environment, pesticide residues remain in crops, soil and rivers, lakes and seas, c...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C29/14C07C33/025C07C67/08C07C69/145
CPCC07C29/14C07C41/30C07C45/42C07C45/69C07C67/08C07C33/025C07C69/145C07C47/24C07C43/17C07C43/15C07C47/21
Inventor 陶云海黄飞江宁王斌沣
Owner 昆明博鸿科技有限公司
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