Formation of 4-Halo-4-nitrocyclohexa-2,5-dienones on nitration of p-halophenols and p-halophenyl acetates

Add time:08/17/2019    Source:sciencedirect.com

Nitration of p-chloro-, p-fluoro-, and p-bromo-phenol or the corresponding p-halophenyl acetates at t-40 °C and below gives the 4-halo-4-nitrocyclohexa-2, 5-dienones in addition to the 4-halo-2-nitrophenols. The dienones isomerize to the nitrophenols at temperatures between −40 °C and 0°C. Nitration of 4-chloro-2-methylphenol or its acetate gives both 4-chloro-2-methyl-4-nitrocyclohexa-2, 5-dienone and 4-chloro-6-methyl-6-nitrocyclohexa-2,4-dienone. 4-Chloro -3-methylphenol and its acetate give 4-chloro-3-methyl-4-nitrocyclohexa-2,5-dienone.

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