Abstract 4-Hydroxybenzofuran and 5-hydroxychroman compounds have been synthesized by heating 2-chloro-2-alkenyl-1, 3-cyclohexanediones, prepared by chlorination of 2-alkenyl- 1, 3-cyclohexanediones with N-chlorosuccinimide, in dimethylformamide-25% hydrogen chloride at 140 C.