Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Production method of alpha-chlorine (2-chlorine) methyl phenylacetate

A kind of technology of methyl phenylacetate and production method, applied in directions such as carboxylic acid halide preparation, organic chemistry, etc., can solve problems such as difficult control of reaction process, high chlorination reaction temperature, low yield in process, and achieve easy reaction process. Control, complete reaction, improve the effect of product purity

Inactive Publication Date: 2013-10-23
TIANJIN HENGTIANLI CHEM
View PDF3 Cites 2 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The method uses o-chlorophenylacetic acid as the starting material, reacts with thionyl chloride to obtain o-chlorophenylacetyl chloride, then reacts with sulfuryl chloride at 124°C to obtain o-chlorophenylacetyl chloride, and then reacts with methanol to obtain α-chlorophenylacetyl chloride (2-chloro) methyl phenylacetate, yield 92%, the technique existence yield of this document report is low, and chlorination reaction temperature is high, the shortcoming that reaction process is difficult for controlling

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Production method of alpha-chlorine (2-chlorine) methyl phenylacetate
  • Production method of alpha-chlorine (2-chlorine) methyl phenylacetate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] (1) Add 170g of o-chlorophenylacetic acid to 450ml of dichloroethane, then add 101g of triethylamine, start stirring, control the temperature at 5-10°C, add 153.5g of phosphorus oxychloride dropwise, and react at room temperature after dropping 1-1.5 hours until thin layer chromatography (TLC) detection shows that o-chlorophenylacetic acid has completely reacted.

[0028] (2) Without purification, the above reaction solution is directly heated slowly to 80-85°C, the reaction solution is refluxed, and the chlorinated reaction of o-chlorophenylacetic acid and phosphorus oxychloride is carried out for 4-5 hours, until thin layer chromatography (TLC) Assays showed the reaction was complete.

[0029] (3) After the chlorination reaction is finished, directly dropwise add 34.5g of methanol and 101g of triethylamine mixed solution in the obtained reaction liquid, control the temperature to be 35-40°C, keep the temperature at 40°C for 1-1.5 hours after the dropwise addition, thi...

Embodiment 2

[0031] (1) Add 170g of o-chlorophenylacetic acid to 550ml of dichloroethane, then add 101g of triethylamine, start stirring, control the temperature at 5-10°C, add 153.5g of phosphorus oxychloride dropwise, and react at room temperature after dropping 1-1.5 hours until thin layer chromatography (TLC) detection shows that o-chlorophenylacetic acid has completely reacted.

[0032] (2) Without purification, the above reaction solution is directly heated slowly to 80-85°C, the reaction solution is refluxed, and the chlorinated reaction of o-chlorophenylacetic acid and phosphorus oxychloride is carried out for 4-5 hours, until thin layer chromatography (TLC) Assays showed the reaction was complete.

[0033] (3) After the chlorination reaction is finished, directly dropwise add 34.5g of methanol and 101g of triethylamine mixed solution in the obtained reaction liquid, control the temperature to be 35-40°C, keep the temperature at 40°C for 1-1.5 hours after the dropwise addition, thi...

Embodiment 3

[0035] (1) Add 170g of o-chlorophenylacetic acid to 300ml of dichloroethane, then add 101g of triethylamine, start stirring, control the temperature at 5-10°C, add 153.5g of phosphorus oxychloride dropwise, and react at room temperature after dropping 1-1.5 hours until thin layer chromatography (TLC) detection shows that o-chlorophenylacetic acid has completely reacted.

[0036] (2) Without purification, the above reaction solution is directly heated slowly to 80-85°C, the reaction solution is refluxed, and the chlorinated reaction of o-chlorophenylacetic acid and phosphorus oxychloride is carried out for 4-5 hours, until thin layer chromatography (TLC) Assays showed the reaction was complete.

[0037] (3) After the chlorination reaction is finished, directly dropwise add 34.5g of methanol and 101g of triethylamine mixed solution in the obtained reaction liquid, control the temperature to be 35-40°C, keep the temperature at 40°C for 1-1.5 hours after the dropwise addition, thi...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention discloses a production method of an alpha-chlorine (2-chlorine) methyl phenylacetate and aims to provide a method which is low-price and available in starting raw materials, high in purity and stable in quality of product, easy and feasible in process, environment-friendly, low in production cost and easy in industrial production. The method comprises the following steps of: using a continuous method, taking chlorophenylacetic acid as a raw material, carrying out acylation reaction for the chlorophenylacetic acid and phosphorus oxychloride at a temperature of 5-10 DEG C for 2-2.5 hours, and subsequently, carrying out chlorination reaction at a temperature of 80-85 DEG C for 4-5 hours, then carrying out esterification reaction with methyl alcohol at a temperature of 35-40 DEG C for 2-2.5 hours, washing a reaction solution by using pure water to remove impurity, drying and filtering a dichloroethane layer, and subsequently, decompressing and concentrating to remove solvents and acquire the alpha-chlorine (2-chlorine) methyl phenylacetate. According to the method, the low-price and available chlorophenylacetic acid is taken as the raw material in the method, so that the production cost is significantly reduced; the phosphorus oxychloride is taken as an acylating agent and a chlorinating agent, so that the purity of the product is improved and the product is environment-friendly. By applying the continuous method, the method is simple and feasible in the technological process, easy to control in the reaction processes and suitable for industrial production.

Description

technical field [0001] The invention relates to a production method of α-chloro(2-chloro)methyl phenylacetate. Background technique [0002] Methyl α-chloro(2-chloro)phenylacetate is an important intermediate in the production of a new anticoagulant drug, clopidogrel bisulfate. [0003] Clopidogrel bisulfate is a new anticoagulant drug, which was first successfully developed in 1986 by the French company Sanofi. Clopidogrel bisulfate is clinically used in patients with recent stroke, myocardial infarction and confirmed peripheral arterial disease. The drug can reduce the occurrence of atherosclerotic events. Combined with aspirin, it is used in patients with non-ST-segment elevation acute coronary syndrome (unstable angina or non-Q wave myocardial infarction). This product does not need to adjust the dose for elderly patients. Clopidogrel bisulfate is widely used in the treatment of severe acute ischemic vascular diseases such as ischemic stroke and myocardial infarction d...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
IPC IPC(8): C07C69/65C07C67/14
Inventor 王洪刚高占友刘长锁马秀玲冯培新
Owner TIANJIN HENGTIANLI CHEM
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com