Abstract
The Grignard reaction of 1-hydroxy-3-methylanthraquinone (II) with methylmagnesium iodide yielded 1, 10-dihydroxy-3, 10-dimethylanthrone (III), which was converted to 3, 10-dimethyl-1-hydroxyanthrone (VI) by reduction with hydriodic acid. Compound VI was also obtained by hydrolysis with hydrochloric acid of 1, 9-diacetoxy-3, 10-dimethyl-anthracene (V), which was prepared by reductive acetylation of III with zinc dust, sodium acetate and acetic anhydride. The method was also found to be applicable to 6-hydroxy-5, 12-naphthacenequinone (IX), thus giving 6-hydroxy-12-methyl-5 (12H)-naphthacenone (XI).
