Electrochimica Acta, Vol.248, 376-387, 2017
A comprehensive study on electrochemical oxidation of 2-acetamidophenol (ortho-acetaminophen). A green galvanostatic method for the synthesis of di-arylsulfonyl-2-acetamidophenol derivatives
Electrochemical oxidation of 2-acetamidophenol (ortho-acetaminophen) in water/ethanol (50/50, v/v) mixture, with different pH values was studied by potential sweep methods (CV and LSV), potential step methods (chronoamperometry and chronocoulometry) and controlled-potential coulometry. The cyclic voltammograms of 2-acetamidophenol show a well-defined anodic peak with different potentials, over the studied pH range (1-13). The Pourbaix diagram for 2-acetamidophenol comprises three linear segments which indicates the occurrence of different anodic reactions. In addition, the results indicate that electrochemically generated ortho-benzoquinoneimine can be successfully employed as a Michael acceptor in addition reactions with arylsulfinic acids to produce the corresponding bis(arylsulfonyl)acetamidophenols. In this work, some new bis(arylsulfonyl)acetamidophenol derivatives in water/ethanol (50/50, v/v) mixture, with high yields, under green conditions using an environmentally friendly galvanostatic method, are provided. (C) 2017 Elsevier Ltd. All rights reserved.
Keywords:2-Acetamidophenol;Electrochemical oxidation;Bis(arylsulfonyl)acetamidophenol;Green synthesis;Cyclic voltammetry