Efficient Synthesis of a Range of 1-Hydroxy-2-(1-Alkyloxymethyl)-9,10-Anthraquinone Derivatives

Five new 1-hydroxy-2-(1-alkyloxymethyl)-9,10-Anthraquinones (9a-e) have been prepared. Selective nitration of 2-methyl-9,10-anthraquinone, reduction to the corresponding amine, diazotization and treatment by sulfuric acid solution afforded the 1-hydroxy-2-methyl-9,10-anthraquinone in good yield as the key intermediate. Reaction with dimethylsulphate/K2CO3 and subsequent monobromination with NBS/CCL4 produced 1-methoxy-2-(bromomethyl)-9,10-anthraquinone. A mixture of HBr/AcOH was used for demethylation. Treatment of hydroxybromo derivatives with different alcohols afforded corresponding ethers in high yields.