Department of Chemistry, Shiraz University, Shiraz, I.R. IRAN
An efficient synthesis of the 1-hydroxy-2-(prop-2'-enyl)9-anthrone is described. Selective nitration of anthraquinone, reduction to the corresponding amine, diazotization and treatment by sulfuric acid solution afforded the 1-hydroxy-9,10-anthraquinone in good yield as the key intermediate. Reaction with allyl bromide/K2CO3 and subsequent selective reduction accompanied by a Claisen rearrangement produced the title compound in high yield.