Preparation of quinol N-acyl-and quinol ether imines via anodic oxidation of para-substituted anilide derivatives

JS Swenton, TN Biggs, WM Clark

Index: Swenton, John S.; Biggs, Timothy N.; Clark, William M. Journal of Organic Chemistry, 1993 , vol. 58, # 21 p. 5607 - 5614

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Citation Number: 9

Abstract

Anodic oxidation of N-benzoyl-4-methylaniline in 5% aqueous methanol in the presence of sodium bicarbonate affords two major products: 4-methoxy-4-methylbenzoquinol N- benzoylimine, 8a, and a dimer, 4-[N-benzoyl-N-(4-methylphenyl) amino]-4- methylbenzoquinol N-benzoylimine, 9. The ratio of these two products was temperature dependent, and conditions were developed for preparing 8a and 9 in good yield. Using ...