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Method for synthesizing p-methoxyphenylacetic acid

A technology of p-methoxybenzene and methoxyhalobenzene, which is applied in the field of synthesizing p-methoxyphenylacetic acid, can solve the problems of high requirements for reaction equipment and expensive catalysts, achieve low output of three wastes, reduce raw materials and operating costs , the effect of protecting the ecological environment

Inactive Publication Date: 2018-06-22
抚顺东科新能源科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0014] This method needs to use hydrogenation reaction, and the catalyst is expensive, and the requirements for reaction equipment are relatively high

Method used

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  • Method for synthesizing p-methoxyphenylacetic acid
  • Method for synthesizing p-methoxyphenylacetic acid
  • Method for synthesizing p-methoxyphenylacetic acid

Examples

Experimental program
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Effect test

Embodiment 1

[0035] Example 1: Add 61 g (1.0 eq) of tert-butyl methyl malonate and 300 milliliters of tetrahydrofuran to the reaction flask under the protection of argon, and add 8.4 g (1.0 eq) of sodium hydride in batches under an ice bath. After the addition is completed, rise to React at room temperature for 1 hour, then slowly add a tetrahydrofuran solution of p-methoxychlorobenzene (50g, 1.0eq) dropwise below 20°C, and the dropwise addition is completed in about 50 minutes. , add 30 ml of water to quench the reaction, concentrate to remove most of the solvent, add 200 ml of concentrated hydrochloric acid, heat up to 100 degrees again and stir the reaction for 16 hours, concentrate to remove most of the water, slowly cool down to crystallize, filter to obtain p-methoxybenzene Acetic acid 49.5g, yield 85%, HPLC: 99.3%.

Embodiment 2

[0036] Example 2: Add 46.6 g (1.0 eq) of tert-butyl methyl malonate and 300 milliliters of tetrahydrofuran to the reaction flask under the protection of argon, and add 6.4 g (1.0 eq) of sodium hydride in batches under an ice bath. React at room temperature for 1 hour, slowly add a tetrahydrofuran solution of p-methoxybromobenzene (50g, 1.0eq) dropwise below 20°C, and complete the dropwise addition in about 50 minutes. After the drop, raise the temperature to 65°C for 10 hours, then cool , add 30 ml of water to quench the reaction, concentrate to remove most of the solvent, add 200 ml of concentrated hydrochloric acid, heat up to 100 degrees again and stir the reaction for 16 hours, concentrate to remove most of the water, slowly cool down to crystallize, filter to obtain p-methoxybenzene Acetic acid 42.6g, yield 96%, HPLC: 99.6%.

Embodiment 3

[0037] Example 3: Add 50.3 g (1.0 eq) of tert-butyl ethyl malonate and 300 milliliters of tetrahydrofuran to the reaction flask under the protection of argon, and add 6.4 g (1.0 eq) of sodium hydride in batches under an ice bath. , raised to room temperature and reacted for 1 hour, slowly added dropwise a tetrahydrofuran solution of p-methoxybromobenzene (50g, 1.0eq) below 20 degrees, and the dropwise addition was completed in about 50 minutes. After the drop, the temperature was raised to 65 degrees for 10 hours , cool down, add 30 ml of water to quench the reaction, concentrate to remove most of the solvent, add 200 ml of concentrated hydrochloric acid, heat up to 100 degrees again and stir the reaction for 16 hours, concentrate to remove most of the water, slowly cool down to crystallize, filter to obtain p-methoxy Phenylacetic acid 42.0g, yield 95%, HPLC: 99.5%.

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Abstract

The invention discloses a method for synthesizing p-methoxyphenylacetic acid. The method comprises the following steps: adding malonate, alkali and p-methoxy halobenzene in a solvent, enabling the p-methoxy halobenzene and the malonate to perform alkylation reaction under the alkali condition, adding water to perform quenching reaction after the reaction is finished, directly acidizing and heatingto perform the decarboxylation hydrolysis reaction after concentrating out most solvent, and then cooling to crystallize, filter and dry, namely obtaining the p-methoxyphenylacetic acid. The method disclosed by the invention has the following advantages: 1, the raw materials used by the method of the invention are easier to obtain and convenient for storing, the raw material and operation cost are greatly reduced; 2, the method disclosed by the invention is less in reaction step, the intermediate reaction process is easy to control and easy for scale production; and 3, the three waste (wastewater, waste solid and waste gas) yield is less, the environment pollution is reduced, and the ecological environment is protected. And meanwhile, the prepared product is high in purity, and the purity can achieve 99% or more; the yield is high and can achieve 95% or more.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis, and in particular relates to a method for synthesizing p-methoxyphenylacetic acid. Background technique [0002] P-methoxyphenylacetic acid is usually a white crystal with a melting point of 84-86°C and is easily soluble in water and various organic solvents. It is an important intermediate in organic synthesis, for example, it is an important intermediate in the synthesis of the antidepressant drug Venlafaxine; it is an important intermediate in the synthesis of the central antitussive drug Dextromethorphan; it is an important intermediate in the synthesis of anti-tumor , an important intermediate of the antifungal drug phenanthridine alkaloids, and also an important intermediate for the synthesis of puerarin and isoflavone cardiovascular drugs. At present, the conventional method of synthesizing p-methoxyphenylacetic acid is as follows: [0003] Method 1: Use p-methoxybenzyl chlori...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C51/09C07C67/343
CPCC07C51/09C07C67/343C07C59/64C07C69/734
Inventor 丁继宇
Owner 抚顺东科新能源科技有限公司
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