Nitration, Amination, and Halogenation of Di-O-methylphloracetophenone

Article abstract of DOI:10.1007/BF00814339

Chlorination of the title compound gave 5'- and 3'-chloro-2'-hydroxy-4',6'-dimethoxyacetophenone.The nitration of its acetate, followed successively by reduction, diazotization, and reaction with cuprous chloride, gave the 3'-substituted series, 2'-acetoxy-4',6'-dimethoxy-3'-nitroacetophenone, 3'-amino-2'-hydroxy-4',6'-dimethoxyacetophenone, and 3'-chloro-2'-hydroxy-4',6'-methoxyacetophenone, respectively.The orientation of substituents in the products was proved.The amino and chloro members of the isomeric 5'-substituted series were available via 2'-hydroxy-4',6'-dimethoxy-5'-phenylazoacetophenone, the product of the reaction of the title compound with benzenediazonium chloride. - Keywords: Acetophenone; Aromatic substitution; Nuclear regioselectivity