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Preparation method of 3,7-dimethyl-3- acetylthio-6,7-epoxy-octanal

A technology of acetylmercapto and dimethyl, which is applied in the field of preparation of sulfur-containing terpenes, can solve the problems of many by-products, low yield, harsh reaction conditions, etc., and achieve the effects of low production cost, simple preparation process and convenient operation

Inactive Publication Date: 2018-09-14
SHANGHAI INST OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

This method has harsh reaction conditions, many by-products and low yield.

Method used

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  • Preparation method of 3,7-dimethyl-3- acetylthio-6,7-epoxy-octanal

Examples

Experimental program
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Effect test

Embodiment 1

[0027] A preparation method of 3,7-dimethyl-3-acetylmercapto-6,7-epoxy-octanal, comprising the following steps:

[0028] (1), at room temperature, 1.21g (98.90%, 5.25mmol) of 3,7-dimethyl-3-acetylmercapto-6-octenal and 1.07g (85.00%, 5.25mmol) of m-chlorobenzeneperformic acid ) was dissolved in 15.00 mL of dichloromethane, stirred and reacted for 4 hours, and the reaction was terminated, and the pH of the reacted solution was adjusted to neutral with a 5% aqueous sodium hydroxide solution by mass fraction to obtain a reaction solution;

[0029] (2), the neutral reaction solution gained in step (1) is extracted with ether, and the organic layer of gained is washed 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 0.98 g of crude product 3,7-dimethyl-3-acetylmercapto-6,7-epoxy-octanal, with a gas chromatography content of 91.36 %, yield 69.95%;

[0030] (3), the crude p...

Embodiment 2

[0034] A preparation method of 3,7-dimethyl-3-acetylmercapto-6,7-epoxy-octanal, comprising the following steps:

[0035](1) At room temperature, mix 1.41g (98.90%, 6.12mmoL) of 3,7-dimethyl-3-acetylmercapto-6-octenal and 1.49g (85.00%, 7.34mmol) of m-chlorobenzeneperformic acid ) was dissolved in 15.00 mL of dichloromethane, stirred and reacted for 4 hours, and the reaction was terminated, and the pH of the reacted solution was adjusted to neutral with a 5% aqueous sodium hydroxide solution by mass fraction to obtain a reaction solution;

[0036] (2), the neutral reaction solution gained in step (1) is extracted with ether, and the organic layer of gained is washed 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 1.20 g of 3,7-dimethyl-3-acetylmercapto-6,7-epoxy-octanal crude product, with a gas chromatography content of 93.56 %, yield 75.35%;

[0037] (3), the crude...

Embodiment 3

[0039] A preparation method of 3,7-dimethyl-3-acetylmercapto-6,7-epoxy-octanal, comprising the following steps:

[0040] (1), at room temperature, 1.51g (98.90%, 6.55mmol) of 3,7-dimethyl-3-acetylmercapto-6-octenal and 1.99g (85.00%, 9.83mmol) of m-chlorobenzeneperformic acid ) was dissolved in 20.00 mL of dichloromethane, stirred and reacted for 8 hours, and the reaction was terminated, and the pH of the reacted solution was adjusted to neutral with a 5% aqueous sodium hydroxide solution by mass fraction to obtain a reaction solution;

[0041] (2), the neutral reaction solution gained in step (1) is extracted with ether, and the organic layer of gained is washed 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 1.47g of crude product 3,7-dimethyl-3-acetylmercapto-6,7-epoxy-octanal, which is tested and obtained by gas phase The chromatographic content is 93.90%, and th...

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Abstract

The invention relates o a preparation method of 3,7-dimethyl-3- acetylthio-6,7-epoxy-octanal. The preparation method comprises following steps: at room temperature, in dichloromethane solvent, 3,7-dimethyl-3- acetylthio-6-octenal and 3-chloroperbenzoic acid are stirred and reacted for 4 to 10h, after reaction, a sodium hydroxide aqueous solution is adopted to adjust the pH value of an obtained reaction solution to 7, ether is adopted for extraction, an obtained organic layer is subjected to drying and filtering, an obtained filtrate is subjected to condensation so as to obtain a 3,7-dimethyl-3- acetylthio-6,7-epoxy-octanal crud product, and silica gel column separation is adopted so as to obtain the 3,7-dimethyl-3- acetylthio-6,7-epoxy-octanal high in purity. Compared with the prior art, the preparation method possesses following advantages: the preparation process is simple; operation is convenient; yield is high; the purity of finished product 3,7-dimethyl-3- acetylthio-6,7-epoxy-octanal is high; the production cost is relatively low; and the preparation method is suitable for industrialized production.

Description

[technical field] [0001] The invention relates to a method for preparing aromatic sulfur-containing terpenes, in particular to a method for preparing 3,7-dimethyl-3-acetylmercapto-6,7-epoxy-octanal. [Background technique] [0002] 3,7-Dimethyl-3-acetylmercapto-6,7-epoxy-octanal is a C13-norprene derivative that widely exists in various flowers, plants and tobacco. The derivative of citral is a very useful spice and pharmaceutical intermediate, especially in the spice, food and pharmaceutical industries, and has a wide range of applications. [0003] However, there are few reports on the synthesis of 3,7-dimethyl-3-acetylmercapto-6,7-epoxy-octanal. In 2015, American scientist Robert J.Canon et al. (Identification, Synthesis, and Characterization of Novel Sulfur-Containing Volatile Compounds from the In-Deph Analysis of Lisbon Lemon Peels[J], 2015,63:1915-1931) used citral as raw material, Under the condition of 0℃, the epoxidation reaction of the double bond is carried out ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D303/34C07D301/14C07D301/32
CPCC07D301/14C07D301/32C07D303/34
Inventor 杨始刚孙玥
Owner SHANGHAI INST OF TECH
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