Anthrahydroquinone (AHQ) and anthrone are alkylated in the Clo position by quinonemethides, generated in situ from p-acetoxybenzyl chlorides, to give adducts 13-15, 24, 25, 28, 29, and 32. Aqueous alkylations of AHQ with methyl vinyl ketone, cinnamaldehyde, and benzyl chloride also produces Clo-substituted 10-hydroxyanthrones. Simple ketones and aldehydes do not, however, alkylate AHQ in aqueous alkali.
