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Direct Substitution of a Hydroxyl Group by a Carboxyl Group at the Benzylic Position in Benzyl Alcohols by Electrochemical Reduction in the Presence of Carbon Dioxide: Improvement Enabling Electrochemical Direct Carboxylation of Benzyl Alcohols even in the Absence of an Electron-withdrawing Group on the Phenyl Ring

Authors :
Mizuki HAYAMA
Hisanori SENBOKU
Source :
Electrochemistry, Vol 91, Iss 11, Pp 112011-112011 (2023)
Publication Year :
2023
Publisher :
The Electrochemical Society of Japan, 2023.

Abstract

Electrochemical carboxylation of benzyl alcohols even in the absence of an electron-withdrawing group on the phenyl ring was successfully carried out by improving our previous electrolysis conditions. Constant current electrolysis of benzyl alcohols including diphenylmethanol in DMSO containing 0.1 mol dm−3 Bu4NBF4 in the presence of carbon dioxide using an undivided cell equipped with a platinum plate cathode and a magnesium rod anode at room temperature resulted in direct substitution of a hydroxyl group by a carboxyl group at the benzylic position to give the corresponding arylacetic acids including diphenylacetic acid in moderate to good yields. Although the effect of DMSO as a solvent is still unclear, the results indicate the potential for a useful, convenient, and eco-friendly synthetic method for arylacetic acids from benzyl alcohols.

Details

Language :
English
ISSN :
21862451
Volume :
91
Issue :
11
Database :
Directory of Open Access Journals
Journal :
Electrochemistry
Publication Type :
Academic Journal
Accession number :
edsdoj.23609115ab34aabb5f3722c0c3f65e5
Document Type :
article
Full Text :
https://doi.org/10.5796/electrochemistry.23-67082