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Method for electrochemically preparing 2-phenylpropionic acid

A phenylpropionic acid, electrochemical technology, applied in chemical instruments and methods, organic chemistry, chemical/physical processes, etc., can solve problems such as human damage

Active Publication Date: 2022-01-28
CHONGQING WERLCHEM FINE CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, this method uses carbon monoxide poisonous gas, which will cause damage to the human body.

Method used

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  • Method for electrochemically preparing 2-phenylpropionic acid
  • Method for electrochemically preparing 2-phenylpropionic acid
  • Method for electrochemically preparing 2-phenylpropionic acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0050] Put 150 grams of 1-phenylchloroethane and 630 grams of dimethyl carbonate in the electrolytic cell equipped with magnesium electrodes and carbon electrodes, add 17.5 grams of tetrabutylammonium bromide, and control the temperature of the electrolytic cell at 35 °C , turn on the DC power supply, adjust the current value at 100-200mA, and continue the electrolysis reaction for 3 hours, and the conversion of 1-phenylchloroethane in the HPLC control is complete;

[0051]Transfer the electrolyte solution into a reaction bottle, cool the reaction solution to room temperature, add 500 milliliters of 10% hydrochloric acid aqueous solution, stir for 10 minutes and leave to separate layers; the upper organic layer is washed three times with 500 milliliters of water;

[0052] Place the above organic layer in a reaction flask, add 100 grams of 10% hydrochloric acid aqueous solution, and heat up to 60-80°C for reaction; during the early stage, the azeotrope of methanol, dimethyl carb...

Embodiment 2

[0057] With the feeding amount, reaction temperature and operation sequence of Example 1, change the current value between 500~600 milliamps, the reaction is obviously accelerated, and the reaction can be completed within 2 hours; subsequent reaction and processing are the same as in Example 1, and finally 132 grams of 2-phenylpropionic acid, HPLC purity greater than 99%.

[0058] 1 H NMR (400MHz, CDCl 3 , TMS) δ: 1.54 (d, 3H, J=7.2, CH 3 ),3.77(q,1H,J=7.2,CH),7.32-7.35(m,4H,Ph),11.6-11.8(br s,1H,OH); mass spectrum(70eV)m / z(relativeintensity): 150(M+,29),106(11),105(100),104(5),103(12),79(14),78(6),77(17),51(7).

Embodiment 3

[0060] Put 150 grams of 1-phenylchloroethane and 1050 grams of dimethyl carbonate in the electrolytic cell equipped with magnesium electrodes and carbon electrodes, add 17.5 grams of tetrabutylammonium bromide, control the temperature of the electrolytic cell at 40 °C, and start DC power supply, adjust the current value between 400 ~ 500 milliamps, continue the electrolysis reaction for 3 hours, and the conversion of 1-phenylchloroethane in the HPLC is complete; the follow-up reaction is the same as in Example 1, and finally 152 grams of 2-phenylpropionic acid are obtained , HPLC purity greater than 99%.

[0061] 1 H NMR (400MHz, CDCl 3 , TMS) δ: 1.54 (d, 3H, J=7.2, CH 3 ),3.77(q,1H,J=7.2,CH),7.32-7.35(m,4H,Ph),11.6-11.8(br s,1H,OH); mass spectrum(70eV)m / z(relativeintensity): 150(M+,29),106(11),105(100),104(5),103(12),79(14),78(6),77(17),51(7).

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Abstract

The invention provides a method for electrochemically preparing 2-phenylpropionic acid, and belongs to the technical field of organic synthesis. The method comprises the following steps: (1) in the presence of a phase transfer catalyst, carrying out electrochemical reaction by taking 1-phenyl chloroethane and dimethyl carbonate as reaction raw materials and magnesium as a consumable electrode to obtain 2-phenyl methyl propionate; and (2) mixing the 2-phenyl methyl propionate with inorganic acid, and carrying out hydrolysis reaction to obtain 2-phenylpropionic acid. According to the invention, 1-phenyl chloroethane and dimethyl carbonate are taken as reaction raw materials, the toxicity is extremely low, and dimethyl carbonate is taken as a reaction raw material and a reaction solvent, so that the use of other organic solvents can be avoided, and the method is more environment-friendly; an electrochemical reaction mode is adopted, so that reaction conditions are mild, high-temperature and high-pressure reaction conditions are avoided, and the method has very high industrial application value; and the 2-phenylpropionic acid obtained by the method provided by the invention has relatively high yield and purity.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a method for electrochemically preparing 2-phenylpropionic acid. Background technique [0002] 2-Phenylpropionic acid is a key intermediate in the synthesis of loxoprofen sodium. Loxoprofen sodium is a non-steroidal anti-inflammatory analgesic drug developed by Sankyo in Japan in 1986. The drug has strong analgesic effect and small gastrointestinal side effects. Since the drug was launched on the market, it has been made into various types of preparations. At present, it has gradually become the first-line drug in the thermal analgesic drug market, and the market capacity has become larger and larger. [0003] [0004] 2-Phenylpropionic acid structure [0005] As a key intermediate of loxoprofen sodium, 2-phenylpropionic acid has a direct impact on the quality and price of loxoprofen sodium. How to better synthesize 2-phenylpropionic acid is the key to solve the p...

Claims

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Application Information

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IPC IPC(8): C07C51/09C07C51/44C07C57/30B01J31/02C25B3/07
CPCC07C51/09C07C51/44B01J31/0239C25B3/07B01J35/33C07C57/30
Inventor 胡开波汪令节杨冰吴伟朱甄珍魏孝强
Owner CHONGQING WERLCHEM FINE CHEM
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