Abstract
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 availablevia 2′-hydroxy-4′,6′-dimethoxy-5′-phenylazoacetophenone, the product of the reaction of the title compound with benzenediazonium chloride.
Zusammenfassung
Chlorierung der Titelverbindung gab 5′- und 3′-Chlor-2′-hydroxy-4′,6′-dimethoxyacetophenon. Die Nitrierung des Acetats, gefolgt von Reduktion, Diazotierung und Reaktion mit CuCl ergab die 3′-substituierte Reihe: 2′-Acetoxy-4′,6′-dimethoxy-3′-nitroacetophenon, 3′-Amino-2′-hydroxy-4′,6′-dimethoxyacetophenon und 3′-Chlor-2′-hydroxy-4′,6′-dimethoxyacetophenon. Die Orientierung der Substituenten wird diskutiert. Die Amino- und Chlorderivate der isomeren 5′-substituierten Reihe sind über 2′-Hydroxy-4′,6′-dimethoxy-5′-phenylacetophenon zugängig, dem Produkt der Reaktion der Titelverbindung mit Phenyldiazoniumchlorid.
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Acton, J.P., Donnelly, D.J. & Donnelly, J.A. Nitration, amination, and halogenation of Di-O-methylphloracetophenone. Monatsh Chem 113, 73–79 (1982). https://doi.org/10.1007/BF00814339
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DOI: https://doi.org/10.1007/BF00814339