Method for synthesizing 5-alkyl-resorcin

A technology of resorcinol and alkyl, which is applied in the field of preparation of 5-alkylresorcinol, can solve the problems of high price, low yield, serious environmental pollution of reaction waste, etc.

Inactive Publication Date: 2009-12-02
EAST CHINA UNIV OF SCI & TECH +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The reaction in each step of this method is a classic reaction, and the yield is stable, but the reaction steps are long, the reaction waste is serious to the environment, corrosive to the equipment, and the raw material cost is high
[0008] (3) Using 5-alkyl-1,3-cyclohexanedione as a raw material, under the action of trifluoroacetic anhydride, the target product was obtained through reactions such as sulfonation, isomerization, and hydrolysis (Synthesis, 1992, 12 , 1287-1291), the large amount of acid liquid that this method synthesizes 5-alkylresorcinol to produce is serious to environmental pollution, and trifluoroacetic anhydride property is active, and is expensive, is not suitable for suitability for industrialized production
Although the synthesis steps of this method are short, the conditions of high temperature alkali fusion reaction are difficult to control and the yield is not high during industrial production

Method used

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  • Method for synthesizing 5-alkyl-resorcin
  • Method for synthesizing 5-alkyl-resorcin
  • Method for synthesizing 5-alkyl-resorcin

Examples

Experimental program
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Embodiment 1

[0028] Mix 13ml of 2% NaOH aqueous solution with 40ml of acetone, stir at room temperature for 1 hour, then slowly add 20g of 40% acetaldehyde aqueous solution dropwise thereto, keep the temperature at 15-20°C, and react for 1.5 hours. Acetone was recovered by atmospheric distillation, and the residual liquid (20ml×3) was extracted with dichloromethane, dried over anhydrous sodium sulfate and concentrated to obtain orange-yellow liquid 4-hydroxy-2-pentanone. Add 20 g of 4-hydroxy-2-pentanone and 2 g of phosphoric acid into 18 ml of toluene, heat to reflux, react for 3 h, distill off the azeotrope of toluene and water under normal pressure, and then distill off the light yellow fraction under reduced pressure to obtain 3- Penten-2-one, dried over anhydrous sodium sulfate. The mixed solution of 3-penten-2-one 8.4g and dimethyl malonate 16.5g in N 2 Drop it into 65ml of 10% sodium methoxide / methanol solution under protection, raise the temperature to reflux, react for 3h, recove...

Embodiment 2

[0032] 5%K 2 CO 3 Mix 150ml of aqueous solution with 300ml of acetone, stir at room temperature for 1h, then slowly add 150g of 40% acetaldehyde aqueous solution to it dropwise, keep the temperature at 15-20°C, and react for 3h. Acetone was recovered by atmospheric distillation, and the residue (150ml×3) was extracted with dichloromethane, dried over anhydrous sodium sulfate and concentrated to obtain orange-yellow liquid 4-hydroxyl-2-pentanone, and 4-hydroxyl-2-pentanone Add 40g of sulfuric acid and 3g of toluene to 36ml of toluene, heat to reflux, react for 3h, distill the azeotrope of toluene and water under normal pressure, and then distill off the light yellow fraction under reduced pressure to obtain 3-penten-2-one, anhydrous Na2SO4 dried. The mixed solution of 3-penten-2-one 16g and dimethyl malonate 32g in N 2 Drop it into 130ml of 10% sodium methoxide / methanol solution under protection, heat up to reflux, react for 3h, remove methanol, dissolve the residue in 150ml...

Embodiment 3

[0035] 10% K 2 CO 3 Mix 50ml of aqueous solution with 200ml of acetone, stir at room temperature for 1 hour, then slowly add 80g of 40% acetaldehyde aqueous solution to it dropwise, keep the temperature at 15-20°C, and react for 2 hours. The acetone was recovered by atmospheric distillation, and the residue was extracted with dichloromethane (100ml×3), dried over anhydrous sodium sulfate and concentrated to obtain orange-yellow liquid 4-hydroxy-2-pentanone. Add 30g of 4-hydroxy-2-pentanone and 1g of DBU to 27ml of toluene, heat to reflux, react for 2h, distill the azeotrope of toluene and water under normal pressure, and then distill off the light yellow fraction under reduced pressure to obtain 3- Penten-2-one, dried over anhydrous sodium sulfate. The mixed solution of 24 g of 3-penten-2-one and 48 g of dimethyl malonate was placed in N 2 Drop it into 130ml of 10% sodium methoxide / methanol solution under protection, raise the temperature to reflux, react for 3h, recover me...

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PUM

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Abstract

The invention relates to a method for preparing 5-alkyl-resorcin, which comprises the following main steps: taking alpha,beta-unsaturated ketone and dibutylmalonate as raw materials; firstly performing reaction between the alpha,beta-unsaturated ketone and the dibutylmalonate under alkaline condition; and performing bromination, decarboxylation and aromatization on the obtained intermediate to obtain a target product. The method has the advantages of low cost and easy acquisition of used raw materials, concise synthetic route, mild reaction conditions and easy operation in various steps, high overall yield, environmental protection and the like.

Description

technical field [0001] The invention relates to a preparation method of resorcinol derivatives, in particular to a preparation method of 5-alkyl resorcinol. Background technique [0002] 5-Alkylresorcinol, as a class of highly active natural source diphenol compounds, is a widely used pharmaceutical intermediate (such as 5-methylresorcinol is a synthetic anticancer substance resveratrol , 5-methyl-7-hydroxy isoflavone and spice 3,5-dimethoxytoluene are important raw materials, and 5-pentyl resorcinol can be used to prepare and treat AIDS, malignant tumors and diseases caused by retroviruses Drugs for diseases such as human immunodeficiency syndrome). In addition, 5-alkylresorcinols have strong oxidase inhibitory activity and can be used in the processing and storage of fruit and vegetable products. [0003] Said 5-alkyl resorcinol of the present invention, it has structure shown in formula I (R 1 for the alkyl group). [0004] [0005] Existing method that can be used...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C39/08C07C37/00
Inventor 沈永嘉王成云周长凯俞国华叶波叶传永黄鹏张学超封静
Owner EAST CHINA UNIV OF SCI & TECH
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