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Method for synthesizing alpha-chlorine (2-chlorine) methyl phenyl acetate

A technology for the synthesis of methyl phenylacetate and its method, applied in the field of synthesis of α-chlorophenylacetate methyl ester, can solve the problems of many impurities, difficult to remove, impure products, etc.

Active Publication Date: 2009-05-20
重庆莱美隆宇药业有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The product obtained by the inventor according to the above-mentioned literature method is impure, has a lot of impurities, is difficult to remove, and has a very low yield

Method used

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  • Method for synthesizing alpha-chlorine (2-chlorine) methyl phenyl acetate
  • Method for synthesizing alpha-chlorine (2-chlorine) methyl phenyl acetate
  • Method for synthesizing alpha-chlorine (2-chlorine) methyl phenyl acetate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Embodiment 1 Preparation of methyl o-chloromandelate

[0023] Measure 10L of methanol into a 30L reaction kettle, add 1000g of o-chloromandelic acid, stir until completely dissolved, slowly add 500ml of concentrated sulfuric acid dropwise, after the dropwise addition is complete, heat up to 80°C for 3 hours, cool to room temperature; use sodium hydroxide solution Adjust the pH to neutral. 5 L of water was added, and 8 L of ethyl acetate was added for extraction. The ethyl acetate layer was washed with saturated sodium bicarbonate, dried, and concentrated to obtain 920 g of methyl o-chloromandelate.

Embodiment 2

[0024] Example 2 Preparation of α-chloro(2-chloro)methyl phenylacetate

[0025] Add 80g of methyl o-chloromandelate and 38.4g of pyridine into the reaction flask, stir, dissolve, and cool to 0°C. Slowly add 50 g of thionyl chloride dropwise. After the dropwise addition was completed, the ice bath was removed, and the temperature of the reaction solution rose slowly to 40°C. The temperature was controlled at 40° C. and stirring was continued for 1 h, and the reaction was detected by HPLC, and the conversion rate was 100%. Filter and wash the filter residue with ethyl acetate. Combine the filtrate and washing liquid, extract with water to remove impurities, add anhydrous sodium sulfate to remove water, filter to remove solid sodium sulfate residue, and evaporate the solvent from the filtrate under reduced pressure to obtain 87 g of methyl α-chloro(2-chloro)phenylacetate, HPLC purity 99.9%, NMR data: 1 H NMR (CDCl 3 ): δ (ppm) = 3.78 (s, 3H), 5.89 (S, 1H), 7.3-7.6 (m, 4H). ...

Embodiment 3

[0026] Example 3 Preparation of α-chloro(2-chloro)methyl phenylacetate

[0027] Add 80g of methyl o-chloromandelate and 38.4g of pyridine into the reaction flask, stir, dissolve, and cool to 0°C. Slowly add 25 g of thionyl chloride dropwise. After the dropwise addition was completed, the ice bath was removed, and the temperature of the reaction solution rose slowly to 40°C. Stirring was continued at 40° C. for 1 h under temperature control, and the reaction was detected by HPLC with a conversion rate of 48%. Filter and wash the filter residue with ethyl acetate. Combine the filtrate and washing liquid, extract with water to remove impurities, add anhydrous sodium sulfate to remove water, filter to remove solid sodium sulfate residue, and evaporate the solvent from the filtrate under reduced pressure to obtain 80 g of crude product, methyl α-chloro(2-chloro)phenylacetate HPLC purity was 40%.

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Abstract

The invention relates to a synthetic method of Alpha-chloro-(2-chloro) methyl phenyl acetate, pertaining to the field of chemical synthesis. The technical problem to be solved by the invention is that a high-purity synthetic method of the Alpha-chloro-(2-chloro) methyl phenyl acetate with high purity is provided. The technical proposal comprises the steps as follows: pyridine is tanken as a solvent, and O-chloro mandelic acid methyl ester reacts with thionyl chloride under the condition of 25 DEG C to 80 DEG C for 0.5h to 5h, and then filtered. Filtrate is extracted by water for impurity removal, and anhydrous sodium sulfate is added for removing water. Filtering is carried out for removing solid sodium sulfate and the filtrate is depressurized for distilling off the solvent to obtain the Alpha-chloro-(2-chloro) methyl phenyl acetate. The reaction formula is shown as the formula in upper right side.

Description

technical field [0001] The invention relates to a synthesis method of α-chloro(2-chloro)methyl phenylacetate, belonging to the field of chemical synthesis. Background technique [0002] Clopidogrel bisulfate (Clopidogrel Bisulfate), a platelet inhibitor, was successfully researched and developed by the French company Sanofi (Sanofi) in 1986, and its trade name is Plavix (Plavix). Current data show that, as a new type of ADP receptor antagonist, clopidogrel is a safe and effective inhibitor of platelet aggregation. It provides a comprehensive countermeasure for the prevention of atherosclerosis and thrombosis, and it can reduce the risk of acute coronary syndrome when used in combination with cyclooxygenase inhibitors such as aspirin, and provide short-term and long-term cardioprotection. The product was first launched in the United States in March 1998, and then entered the markets of Europe, North America, Australia, Singapore and other countries, and was launched in China...

Claims

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Application Information

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IPC IPC(8): C07C69/65C07C67/307
Inventor 唐小海霍晓方邱宇
Owner 重庆莱美隆宇药业有限公司
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