Nitration of 9,10-Dimethylanthracene and 9,10-Diethylanthracene

Abstract

Abstract 9,10-Dimethylanthracene gave 9-nitromethyl-10-methylanthracene as a major product, when treated with fuming nitric acid in dichloromethane at low temperatures. In contrast, 9,10-diethylanthracene yielded 9-nitro-10-hydroxy-9,10-diethyl-9,10-dihydroanthracene, which in refluxing alcohol was readily converted into 9,10-dialkoxy-9,10-diethyl-9,10-dihydroanthracene. Possible reaction sequences for the side-chain nitration have been discussed.