A method for electrochemically synthesizing optically active 2-phenylpropionic acid

An optically active, phenylpropionic acid technology, applied in electrolytic organic production, electrolytic components, electrolytic processes, etc., can solve the problem of high preparation cost, achieve the effects of low cost, convenient operation, and reduce air pollution

Inactive Publication Date: 2016-08-17
EAST CHINA NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

This reaction requires a chiral auxiliary agent equivalent to the molar equivalent of the substrate, so the preparation cost is relatively high, and not all organic halides can be modified by a chiral auxiliary agent. So far, there is no such thing as an active group containing C-Cl Research and Report on Asymmetric Electrocatalytic Carboxylation of 1-Chloro-1-Phenylethane

Method used

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  • A method for electrochemically synthesizing optically active 2-phenylpropionic acid

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Experimental program
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Effect test

Embodiment 1

[0018] a. Preparation of electrolyte

[0019] Mix 0.5mmol 1-chloro-1-phenylethane 75ul with 1mmol tetraethylammonium iodide 0.2572g and 0.025mmol chiral Co II -(R,R)(salen) catalyst 0.0151g and 0.129mol N,N-dimethylformamide 10mL were mixed into an electrolyte solution, and then placed in a one-chamber electrolytic cell with stainless steel as the cathode and magnesium rod as the anode; The 1-chloro-1-phenylethane, tetraethylammonium iodide, chiral Co II -(R,R)(salen) catalyst and N,N-dimethylformamide are analytically pure, in which: 1-chloro-1-phenylethane is the substrate, tetraethylammonium iodide is the supporting electrolyte, and Sex Co II -(R,R)(salen) is the catalyst, N,N-dimethylformamide is grade molecular sieve dried solvent.

[0020] b. Electrocarboxylation reaction

[0021] Under normal pressure, feed carbon dioxide into the electrolytic cell to saturation, and then use 1.0mA / cm 2 The electric carboxylation reaction is carried out at a constant current dens...

Embodiment 2

[0026] a. Preparation of electrolyte

[0027] Mix 0.5mmol 1-chloro-1-phenylethane 75ul with 1mmol tetraethylammonium iodide 0.2572g and 0.025mmol chiral Co II -(R,R)(salen) catalyst 0.0151g and 0.129mol N,N-dimethylformamide 10mL were mixed into an electrolyte solution, and then placed in a one-chamber electrolytic cell with platinum as the cathode and magnesium rod as the anode; The 1-chloro-1-phenylethane, tetraethylammonium iodide, chiral Co II -(R,R)(salen) catalyst and N,N-dimethylformamide are analytically pure, in which: 1-chloro-1-phenylethane is the substrate, tetraethylammonium iodide is the supporting electrolyte, and Sex Co II -(R,R)(salen) is the catalyst, N,N-dimethylformamide is grade molecular sieve dried solvent.

[0028] b. Electrocarboxylation reaction

[0029] Under normal pressure, feed carbon dioxide into the electrolytic cell to saturation, and then use 1.0mA / cm 2 The electric carboxylation reaction is carried out at a constant current density, an...

Embodiment 3

[0033] a. Preparation of electrolyte

[0034] Mix 0.5mmol 1-chloro-1-phenylethane 75ul with 1mmol tetraethylammonium iodide 0.2572g and 0.025mmol chiral Co II -(R, R) (salen) catalyst 0.0151g and 0.129mol acetonitrile 10mL are mixed into electrolytic solution, then put into the one-chamber electrolytic cell with stainless steel as cathode and magnesium rod as anode; The 1-chloro-1-benzene Ethane, tetraethylammonium iodide, chiral Co II -(R,R)(salen) catalyst and acetonitrile are analytically pure, in which: 1-chloro-1-phenylethane is used as substrate, tetraethylammonium iodide is used as supporting electrolyte, chiral Co II -(R,R)(salen) is catalyst, acetonitrile is grade molecular sieve dried solvent.

[0035]b. Electrocarboxylation reaction

[0036] Under normal pressure, feed carbon dioxide into the electrolytic cell to saturation, and then use 1.0mA / cm 2 The electric carboxylation reaction is carried out at a constant current density, and the carbon dioxide is intro...

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Abstract

The invention discloses an electrochemical synthesis method of 2-phenylpropionic acid with optical activity. The method is characterized by comprising the following steps: mixing 1-chlorine-1-phenylethane with N, N-dimethylformamide or acetonitrile and tetraalkylammonium salt to form an electrolyte solution, by taking a chiral schiff base cobalt complex as a catalyst, carrying out electric carboxylation reaction in the presence of normal pressure saturated carbon dioxide by using constant current or constant potential, carrying out rotary evaporation and extraction on the electrolytic reaction liquid to obtain the 2-phenylpropionic acid with the optical activity. Compared with the prior art, the method disclosed by the invention is simple in process and convenient in operation and has the advantages that the greenhouse-effect gas carbon dioxide can be effectively utilized and the atmospheric pollution is reduced; in the meantime, the conversion of aromatic chlorides and the effective synthesis of chiral matters are realized; the raw materials are low in price and easily available, so that the method is low in cost; a new way is created for the research on the green synthesis of organic matters such as aromatic carboxylic acid derivatives; the method particularly shows an excellent application prospect in the fields of agriculture and drug synthesis and is a process route with great industrial synthesis value.

Description

technical field [0001] The invention relates to the technical field of organic chemical synthesis, in particular to a method for synthesizing optically active 2-phenylpropionic acid by electrochemical asymmetric catalysis. Background technique [0002] Studies on the electrocarboxylation of alkyl halides and aromatic halides have been reported in recent years, and the electrocarboxylation reaction of electrochemically activating and fixing carbon dioxide into various economically competitive chemicals has attracted more and more attention. The carboxylation of compounds containing C-X bonds with carbon dioxide is one of the most effective methods for effectively fixing carbon dioxide as useful substances. Cobalt, nickel, palladium and other complexes can effectively improve the yield of organic halide reduction products as catalysts. In the electrochemical research of halides, asymmetric research is generally less involved, and there are few reports on the asymmetric electr...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C25B3/00
CPCY02A50/20
Inventor 王欢陈宝丽杨恒攀池定惠孙文文隋国娇陆嘉星
Owner EAST CHINA NORMAL UNIV
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