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Preparation method of (E, Z)-2, 4-ethyl decadienoate

A technology of ethyl decadienoate and octenoic acid, which is applied in the field of preparation of ethyl-2,4-decadienoate, can solve the problems of poor stability of phosphine ylide, difficulty in industrial amplification, generation of waste residue, etc. High temperature reaction conditions, simplification of operations, and the effect of improving reaction efficiency

Inactive Publication Date: 2019-05-03
鼎元(天津)生物医药科技有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0011] (3), as shown in formula d, Hoffmann et al. reported a method (Synthesis 1977,681) for preparing (E, Z)-2,4-decadienoic acid ethyl ester by wittig reaction, the method involves The obtained phosphine ylide has poor stability, and trans formyl acrylate needs to be used as the reaction raw material in the reaction, which is not easy to obtain, and a large amount of triphenylphosphine oxide will be produced in the reaction process, which will cause a large amount of waste residue to be produced , not easy for industrial amplification

Method used

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  • Preparation method of (E, Z)-2, 4-ethyl decadienoate

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Embodiment 1

[0041]Synthesis of octenoic acid (compound 1): 250g of malonic acid and 400g of pyridine were mixed and placed in a 10L round-bottomed flask, the system was protected by argon replacement, and then 200g of n-hexanal was gradually added dropwise. After the addition, the system continued Stir the reaction at room temperature for 10 hours. After the reaction, add 3L of 20% phosphoric acid aqueous solution to the system in batches, continue stirring for 1 hour after the addition, and then extract the product with ethyl acetate, collect and combine the extract phases, and add Sodium sulfate water is dried, and after drying, ethyl acetate is removed by rotary evaporation to obtain 200g light yellow liquid, namely octenic acid (compound 1), and the 1H nuclear magnetic spectrum is shown in figure 1 , yield 71%.

Embodiment 2

[0043] Preparation of 2,3-dibromooctanoic acid (compound 2): Weigh 50g of octenoic acid (compound 1) and dissolve it in 500mL of dichloromethane, then gradually add 64g of bromine dropwise, after the addition, the system is stirred at room temperature React for 5 hours. After the reaction, the system is orange-yellow and transparent. Then add 300 mL of 20% sodium bisulfite solution and stir for 10 minutes. The system becomes milky white and opaque. Extract with dichloromethane, collect and combine the extract phases, and add anhydrous sulfuric acid Sodium is dried, and after drying finishes, dichloromethane is removed by rotary evaporation, obtains 70g milky white oily substance, namely 2,3-dibromooctanoic acid (compound 2), and 1H NMR spectrum is shown in figure 2 , yield 66%.

Embodiment 3

[0045] Preparation of 1-bromoheptene: Weigh 10g of 2,3-dibromooctanoic acid and dissolve it in 100mL of N,N-dimethylformamide, then add 3g of sodium bicarbonate, after the addition, the system reacts at 120°C for 2h, and the reaction ends Afterwards, the system was tea-yellow and transparent, and then most of the N,N-dimethylformamide in the system was removed by rotary evaporation, and the residue was diluted and dissolved with dichloromethane, and then washed with saturated sodium chloride solution, and then the organic phase, adding anhydrous sodium sulfate to dry, after drying, spin off the solvent to obtain a yellow oil, which was subjected to distillation to obtain 4g of bright yellow liquid, that is, 1-bromoheptene, 1H nuclear magnetic spectrum see image 3 , yield 67%.

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Abstract

The invention provides a preparation method of (E, Z)-2, 4-ethyl decadienoate. According to the preparation method, n-hexyl aldehyde is taken as an initial raw material, and three step chemical conversion is adopted to prepare a key intermediate 1-bromo heptene; 1-bromo heptene and ethyl acrylate are subjected to coupling reaction under the catalytic effect of a metal catalyst so as to obtain (E,Z)-2, 4-ethyl decadienoate. According to the preparation method, metal catalytic coupling reaction is adopted to replace a step in the prior art that (E, Z)-2, 4-ethyl decadienoate is prepared throughpreparation of an organic copper lithium reagent, water-free oxygen-free harsh conditions are avoided, operation is simplified, reaction efficiency is increased, generation of waste water and waste salt is reduced greatly, equipment investment is reduced, and the preparation method is convenient for industrialization production.

Description

technical field [0001] The invention belongs to the field of perfume preparation, and in particular relates to a preparation method of ethyl (E,Z)-2,4-decadienoate. Background technique [0002] Ethyl (E,Z)-2,4-decadienoate, whose English name is ethyl(2E,4Z)-decadienoate or pearester, has a structural formula as shown in formula a, and is a polysaccharide with a special structure of conjugated double bonds. Unsaturated fatty acids have a sharp aroma like pears, apples and fruits. They are naturally present in plants such as apples, bartlett pears and concord grapes. They are the aroma components of these fruits. A new type of edible spice, widely used in the food industry. In addition, since ethyl (E,Z)-2,4-decadienoate has a special fragrance, it can also be combined with modified starch to make fragrance granules for laundry and cleaning. [0003] [0004] Another important use of ethyl (E,Z)-2,4-decadienoate is as a crop biochemical insecticide for pest control. In...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C67/343C07C69/587
Inventor 苗志伟蔡岩孙波王学
Owner 鼎元(天津)生物医药科技有限公司
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