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Preparation method of alpha-hydroxy-cyclohexanecarboxylic acid

A technology of hydroxycyclohexyl and cyclohexyl formic acid, which is applied in the field of preparation of pharmaceutical intermediates, can solve the problems of extremely demanding process requirements for waste acid treatment, potential safety hazards, safety accidents, etc. Effect

Inactive Publication Date: 2012-09-19
WENZHOU IND SCI RES INST
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This route has simple process, relatively mild operating conditions, and the product quality and yield can meet the requirements of industrialization. It is a relatively mature process route; but the first step of this synthetic route uses sodium cyanide, and it is in acidic Addition reaction with cyclohexanone in the environment is easy to generate highly toxic hydrocyanic acid, which has extremely strict requirements on reaction equipment, worker protection and waste acid treatment process, and a little carelessness will cause major safety accidents
Since the application of α-hydroxycyclohexylcarboxylic acid is becoming more and more extensive, and there are serious safety hazards in the original synthesis process, it is necessary to develop new processes and new methods to improve it

Method used

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  • Preparation method of alpha-hydroxy-cyclohexanecarboxylic acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0015] Add 200g (1mol) of 20% sodium hydroxide solution dropwise to the above system, raise the temperature of the system to 85-90°C, keep it warm for 1h, cool to room temperature, adjust the pH of the system to 2-3 with 20% hydrochloric acid, and then extract it with 200ml of toluene After concentration and crystallization, 36g of the product was obtained. The yield calculated with cyclohexyl formic acid was 70%.

[0016] Embodiment two

Embodiment 2

[0018] Add 120g (0.6mol) of 20% sodium hydroxide solution dropwise to the above system, raise the temperature of the system to 60-70°C, keep it warm for 1h, cool to room temperature, adjust the pH of the system to 2-3 with 20% sulfuric acid, and then extract with 150ml of toluene 2 times, after concentration and crystallization, 31g of the product was obtained. The yield calculated with cyclohexyl formic acid was 72%.

[0019] Embodiment three

Embodiment 3

[0021] Add 318g (0.3mol) of 10% sodium carbonate solution dropwise to the above system, control the temperature of the system at 20-40°C, keep it warm for 2 hours, cool to room temperature, adjust the pH of the system to 2-3 with 20% sulfuric acid, and then extract twice with 150ml of toluene After concentration and crystallization, 26g of the product was obtained. The yield is 60% based on cyclohexyl formic acid.

[0022] Embodiment four

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PUM

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Abstract

The invention relates to a synthesis process of corresponding hydroxy-cyclohexanecarboxylic acid from cycloalkyl formic acid. The method is characterized by performing halogenation on cyclohexanecarboxylic acid, subjecting the cyclohexanecarboxylic acid to hydrolization in an alkaline condition, and obtaining a corresponding hydroxy-cyclohexanecarboxylic acid product through acid neutralization, extraction and distillation. According to the preparation method, usage of highly toxic product of sodium cyanide is avoided and the synthesis process of hydroxy-cyclohexanecarboxylic acid is suitable for industrial application.

Description

Technical field [0001] The present invention involves an important method of preparation of medical intermediates, which specifically involves a method of preparation of a α-hydroxyl cycloidic acid preparing by the cycloidic acid. Background technique [0002] α-hydroxyl cytoprotic acid is an important pharmaceutical intermediate.Rainer Schobert and other synthesis of series 3, 5-two replacement of mongeonalized compounds, antibacterial, antiviral, and antitumor medicine activity ( Eur. J. Org. Chem. 2001, 1951-1958; Eur. J. Org. Chem. 2003, 3637-3647); In addition, alpha-hydroxyl cycle cystate is also an important intermediate of the new type of mite killer screw mite.Screw mite is a non -internal absorbent mite killing agent. Its mite killing mechanism is completely different from the existing various mite killing agents.Wide spectrum, killing the ovaries, long -term effects, low toxicity, rhodine resistance, no resistance and other advantages.It can be used for a variety of re...

Claims

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Application Information

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IPC IPC(8): C07C62/04C07C51/367
Inventor 曾余瑶李宝强蒋晓青
Owner WENZHOU IND SCI RES INST
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