Hydrogen Peroxide → Testosterone

Participants

Reaction Conditions

Reaction Steps

A solution of 33g of testosterone in 1500ml of methanol is prepared and cooled in an ice bath to 3°C. Over an hour period, 191ml of 4N sodium hydroxide and 143ml of 30% hydrogen peroxide are added simultaneously. The mixture is stirred at 3° C for an additional 3 hours after which thin layer chromatography shows that the testosterone has been completely consumed. The mixture is poured into 20 gallons of ice water contain 3 pounds of salt and the title epoxide crysallizes. The crystalline material is filtered with suction and the residue is washed with water on the filter and dried to yield 10.5g of the title compound.

Provenance & Evidence