[CH3:1][C@:2]12[CH2:19][CH2:18][C@H:17]3[C@@H:7]([CH2:8][CH2:9][C:10]4[C@:15]3([CH3:16])[CH2:14][CH2:13][C:12](=[O:20])[CH:11]=4)[C@@H:6]1[CH2:5][CH2:4][C@@H:3]2[C:21]([O:23]C)=[O:22].[OH-].[K+].O.Cl>CO>[CH3:1][C@:2]12[CH2:19][CH2:18][C@H:17]3[C@@H:7]([CH2:8][CH2:9][C:10]4[C@:15]3([CH3:16])[CH2:14][CH2:13][C:12](=[O:20])[CH:11]=4)[C@@H:6]1[CH2:5][CH2:4][C@@H:3]2[C:21]([OH:23])=[O:22]To 2.462 kg. of methyl 4-androsten-3-one-17β-carboxylate in 24.6 l of methanol was added 1.23 kg. of potassium hydroxide in 4.9 l. of water. The reaction mixture was refluxed under nitrogen for 6 hours, and then allowed to cool to room temperature overnight. The mixture was acidified with 3200 ml. of 6 N hydrochloric acid. Most of the product crystallized as fine crystals. Then, 14 l. of water was added in a stream over 30 minutes, which precipitated all of the product. The mixture was aged with stirring for 4 hours at 30° C. The mixture was filtered on a cap funnel and washed with water until the wash water showed neutral. The product was dried in an oven at 50° C. overnight. The product, having a m.p. of 245°-248° C., was obtained in 98% yield (2.313 g.).
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