Chloranil → Hydroquinone

Participants

Reaction Steps

10.0 g. of 17α-hydroxy-15α,16α-methylene-17α-[3-(tetrahydropyran-2-yloxy)propyl]-4-androsten-3-one is heated under reflux in 100 ml. of tert.-butanol with 10.0 g. of chloranil for 18 hours. The mixture is filtered off from the precipitate, which has formed (hydroquinone and unreacted chloranil); the filtrate is diluted with ether, washed with sodium bicarbonate solution and water, dried, and evaporated, thus obtaining 10 g. of crude 17β-hydroxy-15α, 16α-methylene-17α-[3-(tetrahydropyran-2-yloxy)propyl]-4,6-androstadien-3-one.

Provenance & Evidence