Chloranil → 19-Hydroxy-4,6-androstadiene-3,17-dione

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Reaction Steps

19-Hydroxy-4-androstene-3,17-dione and chloranil are dissolved in t-butanol which is rapidly brought to its reflux temperature. The t-butanol is removed by distillation at atmospheric pressure at such a rate that the combined reflux and distillation time equals one hour. The dark pasty residue is triturated with hot chloroform and cooled. The solid is removed by filtration and the filtrate extracted with water, a 2% sodium hydroxide solution and again with water. The organic layer is dried over magnesium sulfate and the solvent removed under vacuum to yield 19-hydroxy-4,6-androstadiene-3,17-dione. This diene so prepared is dissolved in acetone and chilled in an ice bath. Jones reagent is added over a 10 minute period and stirring continued for an additional 45 minutes. The mixture is poured onto water. The solid is filtered and recrystallized from benzene to yield 4,6-androstadiene-3,17,19-trione.

Provenance & Evidence