CHEMICAL AND ELECTROCHEMICAL OXIDATION OF 2,5-DIMETHYLFURAN TO 2,5-DIMETHL-2,5-DIMETHOXYDIHYDROFURAN

2,5-Dimethylfuran has been oxidized to 2,5-dimethyl-2,5-dimethoxydihydrofuran both chemically, with bromine in methanol in the presence of excess sodium carbonate, and electrochemically at a platinum anode. The product is a mixture of geometric isomers which was separated by preparative vpc to the point where each isomer was better than 90% pure. Nmr spectroscopy was used to assign structures to these isomers. Both the chemical and electrochemical oxidations result in a 50:50 mixture of the cis and trans isomers, within experimental error. An additional product of the electrochemical oxidation is 2,5-bis (methoxymethyl) furan, formed in very low yield with sodium methoxide as the electrolyte and in appreciably higher yield with ammonium nitrate as the electrolyte. © 1969, American Chemical Society. All rights reserved.