3beta-Acetoxyandrost-5-en-17-one → HCID 21813599, compound

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Reaction Steps

300 g (0.9 mole) of dehydroepiandrosterone acetate are dissolved in 1160 ml of isopropenyl acetate, whereupon a solution of 4 ml of concentrated sulfuric acid in 100 ml of isopropenyl acetate is added. The temperature of the reaction mixture is raised slowly (in two hours) to the boiling temperature of isopropenyl acetate, and continuously 400 ml of an acetone/isopropenyl acetate mixture are distilled off. After heating and continuous distillation for 6 hours, the solution is cooled to room temperature and added to 10000 ml of ice water, under stirring. The precipitous solution is allowed to stand at 5° to 10° C. for 12 hours, whereupon the precipitate is filtered off, washed acid-free with water, dried at room temperature and the crude product is crystallized from methanol.

Provenance & Evidence