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A kind of preparation method of 4,6(z), 8(e)-macrotriene

A dichloromethane solution technology, applied in 4 fields, can solve the problems of difficult to obtain raw materials and harsh reaction conditions, and achieve the effects of low price, simple preparation process, high yield and purity

Inactive Publication Date: 2014-10-29
SHANGHAI INST OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, although this method has a high yield, it is also a mixture of four isomers of 4,6,8-macrotriene. In addition, heating and pressure operations are required, the reaction conditions are harsh, and the raw materials are not easy to obtain.

Method used

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  • A kind of preparation method of 4,6(z), 8(e)-macrotriene

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] A kind of preparation method of 4,6 (Z), 8 (E)-macrotriene, comprises the following steps:

[0036] (1) Under an ice-water bath, dissolve 1.52g (98.90%, 7.73mmol) of β-ionol in 15.00ml of dichloromethane, and add 1.22g (15.50mmol) of pyridine under stirring. After fully stirring, within 5min Add 10ml of dichloromethane solution of ethyl chloroformate dropwise (1.68g (15.5mmol) of ethyl chloroformate, 10 ml of dichloromethane), after all the addition is completed, continue to stir the reaction at 20-25°C for 6h to end the reaction , and adjust the pH of the solution after the reaction to neutrality with a mass fraction of 5% dilute hydrochloric acid to obtain a reaction solution;

[0037] (2), the neutral reaction solution obtained in step (1) was extracted with ether, and the organic layer obtained was extracted with anhydrous MgSO 4 Dry and filter with filter paper the next day, and the obtained filtrate is evaporated and concentrated by a rotary evaporator to obtain ...

Embodiment 2

[0047] A kind of preparation method of 4,6 (Z), 8 (E)-macrotriene, comprises the following steps:

[0048] (1) Under an ice-water bath, dissolve 1.42g (98.90%, 7.24mmol) of β-ionol in 8.00ml of dichloromethane and 1.14g (14.48mmol) of pyridine. After fully stirring, add dropwise within 5min Dichloromethane solution of ethyl chloroformate 12ml (ethyl chloroformate 0.786g (7.24mmol), dichloromethane 12 ml), continue to stir the reaction at 20-25°C for 6h, end the reaction, and dilute with 5% mass fraction Hydrochloric acid adjusts the pH of the solution after the reaction to neutrality to obtain a reaction solution;

[0049] (2), the neutral reaction solution obtained in step (1) was extracted with ether, and the organic layer obtained was extracted with anhydrous MgSO 4 Dry and filter with filter paper the next day, and the obtained filtrate is evaporated and concentrated by a rotary evaporator to obtain 1.25g of crude product of 4,6(Z),8(E)-macrotriene, the content of gas chr...

Embodiment 3

[0052] A kind of preparation method of 4,6 (Z), 8 (E)-macrotriene, comprises the following steps:

[0053] (1) Under an ice-water bath, dissolve 1.60g (98.90%, 8.16mmol) of β-ionol in 12.00ml of dichloromethane and 1.29g (16.32mmol) of pyridine. After fully stirring, add dropwise within 5min Dichloromethane solution of ethyl chloroformate 12ml (ethyl chloroformate 1.328g (12.24mmol), dichloromethane 12 ml), continue to stir and react at 20-25°C for 6h, adjust the solution with dilute hydrochloric acid with a mass fraction of 5% pH to neutral to obtain a reaction solution;

[0054] (2), the neutral reaction solution obtained in step (1) was extracted with ether, and the organic layer obtained was extracted with anhydrous MgSO 4 Dry and filter with filter paper the next day. The obtained filtrate is evaporated and concentrated by a rotary evaporator to obtain 1.38g of 4,6(Z), 8(E)-macrotriene crude product. After testing, the gas chromatography content is 94.18%, and it is obta...

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Abstract

The invention discloses a preparation method for 4, 6 (Z), 8 (E)-large column triene. Under the condition of ice-water bath, beta-ionol is dissolved in organic solvent of dichloromethane and pyridine, then ethyl chloroformate is dripped in, and reaction is carried out at room temperature. Obtained reaction liquid is adjusted to get neutral hydrogen potential (PH) value through 5% diluted hydrochloric acid, and then is extracted by diethyl ether. Obtained organic layer is dried by anhydrous MgSO4, and then is filtered by filter paper next day. Filter liquid is evaporated and concentrated through a rotary evaporator to obtain a rough product of the 4, 6 (Z), 8 (E)-large column triene. The rough product of the 4, 6 (Z), 8 (E)-large column triene is separated through a silicagel column to obtain highly-purified 4, 6 (Z), 8 (E)-large column triene. The preparation method has the advantages of being simple in preparation process, convenient to operate, and high in yield rate and purity of the final product, namely the 4, 6 (Z), 8 (E)-large column triene, and the like, moreover, the preparation method is low in production cost, and suitable for industrial production.

Description

technical field [0001] The present invention relates to a preparation method of aromatic terpene hydrocarbons, more specifically to a preparation method of 4,6(Z),8(E)-macrotriene. Background technique [0002] 4,6,8-Pillartriene is a kind of C widely present in various flowers, plants and tobacco 13 -Norisoprene derivatives, which are metabolic degradation products of higher terpenoids, have four isomers, namely 4,6(E), 8(E)-macrotriene, 4,6(E) . [0003] The isomer 4, 6(Z), 8(E)-macrotriene is a very useful spice and pharmaceutical intermediate, especially in the spice, food and tobacco industries, and has a wide range of applications. [0004] The first to synthesize 4,6,8-macrotriene was an Australian chemist. In 1982, Whitfield F B and others used p-toluenesulfonic acid and hexamethylphosphoric triamide as catalysts to dehydrate β-ionol to synthesize 4,6,8-macrotriene. β-ionol was reacted with 5% p-toluenesulfonic acid as a catalyst at 20°C for 10 minutes to obtain ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C13/21C07C1/207
Inventor 杨始刚黄红尚利亚
Owner SHANGHAI INST OF TECH