Water → HCID 178445663, compound

Participants

Reaction Conditions

Reaction Steps

Trans-4-n-butylcyclohexanecarboxylic acid (11, 50.0 g, 0.27 mol) was added to a solution of trifluoroacetic anhydride (57.0 g, 0.27 mol) in dry dichloromethane (600 ml) and the resulting solution was stirred for 30 min. at 20° C. Testosterone (7, 78.3 g, 0.27 mol) was then added and the mixture was stirred for a further 2 hr at 20° C. After this period, water (500 ml) was added and the two layers were briskly stirred together for 15 min. The dichloromethane layer was separated and washed successively with saturated NaHCO3 (2×250 ml) and then H2O (250 ml). Evaporation of the solvent gave the crude testosterone ester (139.6 g), as an oil which solidified slowly on standing. The solid was dissolved in anhydrous ethanol (140 ml) by warming and the solution was then cooled to 5° C. and held at this temperature for 2 hr. The precipitated solid was filtered and recrystallised twice more from ethanol (70 ml and 80 ml) to give testosterone trans-4-n-butylcyclohexanecarboxylate (65 g, 99.1%) as a white crystalline solid, m.p. 132-134° C. It was identical with the sample prepared by means of Method A.

Provenance & Evidence