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.