p-Toluenesulfonic acid → 3-Ethoxy-androsta-3,5-dien-17-one

Participants

Reaction Steps

Androstenedione (5 g.) was dissolved in dry benzene (20 ml). Triethyl orthoformate (6 ml) was added, followed by p-toluenesulphonic acid (250 mg) and the solution left at room temperature for ten minutes. The benzene solution was washed with aqueous sodium hydroxide (10%), followed by water, dried (anhydrous Na2SO4) and evaporated under reduced pressure to give a pale yellow solid (5.5 g.). This solid was recrystallized from ethanol to give 3-ethoxy-androsta-3,5-dien-17-one (4.3 g.) as white needles, m.p. 146°-149°. ##STR13##

Provenance & Evidence