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Preparation method of 2-methyltetrahydrofuran-3-thiol

A technology of methyltetrahydrofuran and mercaptan, applied in the direction of organic chemistry and the like, can solve the problems of high cost of treatment of three wastes, difficult rectification impurities in products, many unqualified products, etc., and achieves the effects of high product quality, easy purification, and less three wastes

Active Publication Date: 2020-11-17
JINAN ENLIGHTEN BIOTECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0011] The inventor found through experimentation that the process route is relatively long, the treatment is relatively cumbersome, and the cost of the three wastes is relatively high. The obtained product contains impurities that are difficult to rectify, resulting in many unqualified products, and the problem is more obvious when the production is scaled up.

Method used

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  • Preparation method of 2-methyltetrahydrofuran-3-thiol
  • Preparation method of 2-methyltetrahydrofuran-3-thiol
  • Preparation method of 2-methyltetrahydrofuran-3-thiol

Examples

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preparation example Construction

[0026] The synthesis process of the preparation method provided by the invention only needs two steps, the operation is simple, the three wastes are less, and the yield is high.

[0027] The solvent for preparing intermediate 1 from bread ketone through vulcanization reaction can be tetrahydrofuran, dichloromethane, acetonitrile, toluene, etc. However, in the process of vulcanizing bread ketone with a vulcanizing agent, the viscosity of the solution will increase, and even the phenomenon that the material becomes spherical , thereby affecting the complexity of the purification process and at the same time affecting the product yield. In some examples of this embodiment, the solvent for preparing intermediate 1 from bread ketone is acetonitrile. It is found through experiments that when acetonitrile is used as the solvent, the purification process is simple and the product yield is further improved.

[0028] In some examples of this embodiment, the vulcanizing agent is P 2 S ...

Embodiment 1

[0040] In a 1L clean four-necked bottle equipped with stirring and a thermometer, add 200g (2mol) of bread ketone as the raw material, add 600g of tetrahydrofuran, start stirring, heat the oil bath slowly to 50°C, and add P 2 S 5 310g (0.7eq) was controlled at 55°C, added and kept warm at 50°C for 5 hours. The solid was in a dispersed state at the beginning, and then gradually became sticky, adhered to the wall and agglomerated. The reaction was monitored by TLC. The developer was (ethyl acetate: petroleum ether = 1 : 5) After the reaction is finished, lower the temperature to 10° C., add dropwise saturated aqueous sodium carbonate solution to adjust the pH to 7, continue to stir for 10 minutes, remove the solid by suction filtration, add 100 g of water to the filtrate, and extract and stand for layering with dichloromethane 150*3. Combined organic phases were precipitated to obtain intermediate 1 crude product 170g, GC content 90%, yield 70% MS (ES + ): M / Z=116 (M + ).

...

Embodiment 2

[0043]In a 1L clean four-necked bottle equipped with stirring and a thermometer, add 200g (2mol) of the raw material bread ketone, add 600g of dichloromethane, start stirring, heat the oil bath slowly to 40°C, and add P 2 S 5 310g (0.7eq) was controlled at 45°C, added and kept warm at 50°C for 5 hours. The solid was in a dispersed state at the beginning, and then gradually became sticky, adhered to the wall and agglomerated. The reaction was monitored by TLC. The developer was (ethyl acetate: petroleum ether = 1 : 5) After the reaction is finished, lower the temperature to 10° C., add dropwise saturated aqueous sodium carbonate solution to adjust the pH to 7, continue to stir for 10 minutes, remove the solid by suction filtration, add 100 g of water to the filtrate, and extract and stand for layering with dichloromethane 150*3. Combine the organic phases and remove the solvent to obtain 200g of intermediate 1 crude product, GC content 90%, yield 85% MS (ES + ): M / Z=116 (M +...

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Abstract

The invention discloses a preparation method of 2-methyltetrahydrofuran-3-thiol. The method comprises the following steps: carrying out vulcanization reaction on 2-methyltetrahydrofuran-3-one servingas a raw material by using a vulcanization reagent to obtain an intermediate 1, and carrying out reduction reaction on the intermediate 1 to obtain the 2-methyltetrahydrofuran-3-thiol. According to the method disclosed by the invention, 2-methyltetrahydrofuran-3-thiol is prepared by directly vulcanizing 2-methyltetrahydrofuran-3-one and then carrying out reduction and two steps, so that the methodis short in reaction route, mild in reaction condition, simple to operate, less in three wastes, high in yield, easy to purify and high in product quality.

Description

technical field [0001] The invention relates to a preparation method of 2-methyltetrahydrofuran-3-mercaptan. Background technique [0002] The information disclosed in this background section is only intended to increase the understanding of the general background of the present invention, and is not necessarily taken as an acknowledgment or any form of suggestion that the information constitutes the prior art already known to those skilled in the art. [0003] With the improvement of living standards, people's demand for diversified food tastes is increasing, and the status of food flavors in food is becoming more and more important. Among them, sulfur-containing spices play a vital role in improving the taste of food due to their low aroma threshold, strong characteristics, and small dosage. Among them, 2-methyltetrahydrofuran-3-thiol is widely used. A sulfur-containing spice. [0004] The chemical formula of 2-methyltetrahydrofuran-3-thiol is: [0005] 2-Methyltetrah...

Claims

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Application Information

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IPC IPC(8): C07D307/18
CPCC07D307/18
Inventor 张绪猛李新毛浙徽王文新种道皇汪运光
Owner JINAN ENLIGHTEN BIOTECH CO LTD
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