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Method for preparing optical pure chiral o-chloromandelic acid

An o-chloromandelic acid and chiral technology, applied in the field of preparing optically pure chiral o-chloromandelic acid, can solve the problems of only 81.1% optical purity, increased raw material cost, harsh reaction conditions, etc. Success rate, cheap effect

Inactive Publication Date: 2017-08-25
枣阳市残联福利生物化工厂
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the prior art, in the process of preparing o-chloromandelic acid, the reaction step is longer and the reaction conditions are harsh, so the cost of raw materials is increased, and the yield is 29.4%, and the optical purity of the resulting product is only 81.1%.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] The present invention proposes a method for preparing optically homochiral o-chloromandelic acid, comprising the following steps:

[0022] S1, select o-chlorobenzaldehyde, catalyst and chiral resolving agent as raw materials, and the mol ratio of o-chlorobenzaldehyde, catalyst and chiral resolving agent is 2:0.5:0.5, and the raw material is sealed and preserved to prevent its previous undesired reaction;

[0023] S2, above-mentioned o-chlorobenzaldehyde is placed in the reactor, and place 6min under the environment of 15 degrees Celsius, then slowly add a catalyst therein, and the temperature is raised to 35 degrees Celsius, until reaction occurs;

[0024] S3, after completion, pass halogen gas into the reactor treated in S2, mix and stir, and heat to 60 degrees Celsius, carry out halogenation, slowly carry out stirring and cooling, after the solid is separated out, suction filtration, dry, and collect the solid;

[0025] S4, carry out hydrolysis reaction with the soli...

Embodiment 2

[0036] The present invention proposes a method for preparing optically homochiral o-chloromandelic acid, comprising the following steps:

[0037] S1, select o-chlorobenzaldehyde, catalyst and chiral resolving agent as raw materials, and the mol ratio of o-chlorobenzaldehyde, catalyst and chiral resolving agent is 2:0.5:0.5, and the raw material is sealed and preserved to prevent its previous undesired reaction;

[0038] S2, above-mentioned o-chlorobenzaldehyde is placed in the reactor, and place 7min under the environment of 16 degrees Celsius, then slowly add a catalyst therein, and the temperature is raised to 40 degrees Celsius, until reaction occurs;

[0039] S3, after completion, pass halogen gas into the reactor after processing in S2, mix and stir, and heat to 65 degrees Celsius, carry out halogenation, slowly carry out stirring and cooling, after the solid is separated out, suction filtration, dry, collect solid;

[0040] S4, carry out hydrolysis reaction with the sol...

Embodiment 3

[0051] The present invention proposes a method for preparing optically homochiral o-chloromandelic acid, comprising the following steps:

[0052] S1, select o-chlorobenzaldehyde, catalyst and chiral resolving agent as raw materials, and the mol ratio of o-chlorobenzaldehyde, catalyst and chiral resolving agent is 2:0.5:0.5, and the raw material is sealed and preserved to prevent its previous unwanted reaction;

[0053] S2, above-mentioned o-chlorobenzaldehyde is placed in the reactor, and place 8min under the environment of 18 degrees Celsius, then slowly add a catalyst therein, and the temperature is raised to 45 degrees Celsius, until reaction occurs;

[0054] S3, after completion, pass halogen gas into the reactor after processing in S2, mix and stir, and heat to 70 degrees Celsius, carry out halogenation, slowly carry out stirring and cooling, after precipitation of solid, suction filtration, dry, collect solid;

[0055]S4, carry out hydrolysis reaction with the solid col...

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Abstract

The invention discloses a method for preparing optical pure chiral o-chloromandelic acid. The method comprises the following steps of putting o-chlorobenzaldehyde into a reactor, slowly adding a catalyst, introducing halogen gas into the treated reactor, mixing, stirring, collecting a solid, and carrying out hydrolysis reaction on the collected solid to generate a reaction liquid; adding inorganic acid to the water solution, heating the water solution to 150-200 DEG C to evaporate and dewater the moisture in the water solution, and removing ammonia chloride in the reaction liquid; transferring a chiral resolving agent to a first solution, and re-crystallizing under the condition of 60-75 DEG C to obtain crude o-chloromandelic acid; and further cooling the crude o-chloromandelic acid to be less than or equal to 0 DEG C, re-crystallizing by using methylbenzene, and drying the crude o-chloromandelic acid under the condition of 60-80 DEG C to obtain the optical pure chiral o-chloromandelic acid. According to the method, the production cost is significantly reduced, the reaction time can be effectively shortened, and the success rate is improved.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a method for preparing optically homochiral o-chloromandelic acid. Background technique [0002] o-Chloromandelic acid, also known as α-hydroxy-o-chlorophenylacetic acid, has a relative molecular mass of 186.5 and has two enantiomeric configurations, R-type and S-type. It is widely used in pharmaceutical production, chemical intermediates and other fields. application. Among them, (R)-o-chloromandelic acid can synthesize a new safe and efficient anti-platelet aggregation drug clopidogrel, so it has a broad market. It is clinically used to prevent atherosclerosis in patients with myocardial infarction, stroke or a history of peripheral arterial disease with good results. With the success of clopidogrel and the further development of optically pure o-chloromandelic acid, the consumption of chiral o-chloromandelic acid is increasing day by day, and the market demand is e...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C51/00C07C51/43C07C59/56C07B57/00
CPCC07C51/00C07B57/00C07B2200/07C07C51/43
Inventor 曹亮
Owner 枣阳市残联福利生物化工厂