The nitration in acetic acid of 9-Acetoxy- and 9-Methoxy-10-phenylanthracenes

Abstract

Nitration of 9-acetoxy-10-phenylanthracene (1a) in acetic acid gives the nitro diacetate (2a), 10-acetoxy-10-phenylanthrone (3), 10-hydroxy- 10-phenylanthrone (4) and 10-nitro-10-phenylanthrone (5), the 10- acetoxy (3) and 10-hydroxy (4) compounds being formed from the unstable nitro diacetate (2a). Nitration ipso to the acetoxy group in (1a) is therefore the major (c. 80%) reaction pathway. Nitration of the 9- methoxy compound (1b) gives predominantly (> 80%) the 10-nitro compound (5) and small amounts of the 10-acetoxy compound (3).