15 g of a mixture of 4β,5-epoxy-etiocholane-17β-ol-3-one and 4β,5-epoxyandrostane-17β-ol-3-one, dissolved in 375 ml chloroform, are treated with a
stream of gaseous HCl at room temperature for about 2 h. The chloroform
solution is neutralized with a sodium bicarbonate solution, washed with water
and dried. The residue is crystallized from benzene or aqueous methanol and
9 g of needle-shaped crystals of 4-chloro-testosterone, melting point 186°-
188°C, are obtained. Upon concentrating the mother-liquor, 3.2 g of this
product, melting point 180°-184°C, are covered.
1 g 4-chloro-testosterone are acetylated with 1 ml acetic anhydride and 5 ml
pyridine at room temperature for 16 h. Ice is added to the solution, and the
precipitate is filtered off and recrystallized from chloroform-ethanol; 1 g 4-
chloro-testosterone-acetate, melting point 228°-230°C, is obtained.
