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Thymol, and preparation method and pharmaceutical composition thereof

A technology for thymol and cresol, which is applied in the field of organic compound preparation, can solve the problems of high equipment requirements, low selectivity, difficult separation and the like, and achieves the effects of high total yield, mild scheme conditions, and cheap and easy-to-obtain raw materials

Active Publication Date: 2018-11-30
ZHANGZHOU SHUIXIAN PHARMA CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The purpose of the present invention is to provide a kind of preparation method of thymol in order to overcome the problems of high equipment requirement, low selectivity, many side reactions and difficult separation in the existing synthetic thymol, which has selectivity Strong, short reaction time, mild reaction process, strong controllability, etc.

Method used

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  • Thymol, and preparation method and pharmaceutical composition thereof

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preparation example Construction

[0040]In the preparation method of thymol provided by the present invention, the first step is: condensation reaction of m-cresol and ethyl acetoacetate to obtain 4,7-dimethylcoumarin. The present invention has no special limitation on the conditions for the condensation reaction to occur. For example, existing solid superacid catalysis and acidic zeolite catalysis can be used, and the reaction can be carried out in a solvent environment or in a solvent-free environment. As a preferred scheme of the present invention, m-cresol and ethyl acetoacetate are reacted at 110-120° C. for 4-6 hours under the action of Lewis acid and mixed solvent to obtain 4,7-dimethylcoumarin, m-cresol and ethyl acetoacetate The ratio of the amount of ethyl acetoacetate is 1:1.0-10, preferably 1:1.0-3.0, and most preferably 1:1.2-2.0. The mass ratio of m-cresol to Lewis acid is 1:0.5-5.0, preferably 1:1.0-4.0, and most preferably 1:1.5-3.0. The Lewis acid is independently aluminum trichloride or tita...

Embodiment 1

[0056] Prepare thymol according to the following steps, the reaction process is as follows figure 1 Shown:

[0057] Step 1: Dichloromethane (1.2kg) was added into a 5L four-necked flask, and aluminum trichloride (0.94kg) was added to obtain a suspension. Ethyl acetoacetate (0.54kg) was slowly and uniformly added to the reactor; after addition, m-cresol (0.3kg) was added. Add dioxane (0.8kg), slowly raise the temperature to collect dichloromethane to T=110-112°C, stop collecting dichloromethane, and keep warm at 110-120°C for 5 hours. Cool down and add dichloromethane (2.2kg), then add purified water (1.8kg); keep warm at 20-30°C for liquid separation for 30 minutes, and separate the organic phase; add purified water (0.6kg) to the organic phase, stir for 15 minutes, and let stand Separation for 60min. The organic phase was transferred to a still, and concentrated under reduced pressure until there was no distillate; ethanol (0.5 kg) was added, and stirred at 0-5°C for 1 h. ...

Embodiment 2

[0065] Step 1: Pour methylene chloride (6kg) into a glass reactor, add aluminum trichloride (4.7kg) to obtain a suspension. Ethyl acetoacetate (2.7kg) was slowly and uniformly added to the reactor; after addition, m-cresol (1.5kg) was added. Add toluene (4.5kg), slowly raise the temperature to collect dichloromethane to T=110-112°C, stop collecting dichloromethane, and keep warm at 110-120°C for 5 hours. Cool down and add dichloromethane (11kg), then add purified water (9kg); keep warm at 20-30°C for liquid separation for 30 minutes, and separate the organic phase; add purified water (3kg) to the organic phase, stir for 15 minutes, and stand for liquid separation for 60 minutes . The organic phase was transferred to a still, and concentrated under reduced pressure until there was no distillate; ethanol (2.5kg) was added, and stirred at 0-5°C for 1h. Blow out, filter with suction, rinse the filter cake with cold ethanol (1.5kg) (below 10°C). The filter cake is air-dried at 6...

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Abstract

The invention discloses thymol, and a preparation method and pharmaceutical composition thereof. The preparation method comprises the steps of: conducting a condensation reaction on m-cresol and ethylacetoacetate to obtain 4,7-dimethylcoumarin, performing hydrolysis decarboxylation on the 4,7-dimethylcoumarin under conditions of a strong alkali and high temperature to obtain an organic phase C containing 5-methyl-2-(prop-1-en-2-yl)phenol, and reducing the organic phase C to obtain thymol. The preparation method of thymol disclosed by the invention is mild in conditions, does not need specialreaction equipment, and facilitates industrial production. With the preparation method, position selectivity is high, almost no position isomer is generated, the separated product is high in purity, the total yield is high and the product quality accords with current drug declaration requirements.

Description

technical field [0001] The invention relates to an organic compound preparation technology, in particular to thymol, a preparation method and a pharmaceutical composition thereof. Background technique [0002] Thymol is a preservative and an antioxidant, but also a food flavoring spice, and also a primary raw material for the synthesis of many chemicals, such as the hydrogenation of thymol to synthesize menthol. Thymol is originally an antibacterial active ingredient extracted from Thymus serpyllum L., a Chinese herbal plant of the Labiatae family, and is a representative hydroquinone compound. It has strong antibacterial effect, wide antibacterial spectrum, low toxicity, and has inhibitory or killing effects on Staphylococcus aureus, typhoid bacillus, Pseudomonas aeruginosa, Proteus, etc. Its bactericidal effect is stronger than phenol, and its toxicity is low. Throat mucous membrane has bactericidal and fungicidal effects, has antiseptic and local anesthetic effects on ca...

Claims

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Application Information

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IPC IPC(8): C07C39/06C07C37/00C07C37/055C07C39/19C07D311/16A61K31/05A61P31/04A61P31/10A61P17/18
CPCA61P17/18A61P31/04A61P31/10C07C37/003C07C37/0555C07C39/06C07D311/16C07C39/19
Inventor 于凯姜玉岗王永广葛志敏李智祥林聪明
Owner ZHANGZHOU SHUIXIAN PHARMA CO LTD
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