Hydrochloric Acid → HCID 178445063, compound

Participants

Reaction Steps

4-[4-(4-pentylbicyclo[2.2.2]octyl)penyl]cyclohexanone (1.5 g, 4.3 mmol) and a mixture of 9:1 methanol/ether (25 cm3) is added dropwise to a freshly prepared mixture of sodium borohydride (1.2 g, 8.5 mmol) and a mixture of 9:1 methanol/ether (25 cm3) at 0° C. When the addition is complete, the reaction mixture is stirred overnight at room temperature. A 25 per cent hydrochloric acid solution is added carefully to the reaction mixture, which was extracted into ethyl acetate (3×50 cm3). The combined organic extracts are washed with water (2×500 ml) and dilute sodium carbonate solution (2×500 ml), dried (MgSO4), filtered and then evaporated down. The residue is purified by column chromatography on silica gel using a 7:3 hexane/ethyl acetate mixture as eluent and recrystallisation from ethanol to yield the pure 1-[4-(trans-4-hydroxycyclohexyl)phenyl]-4-pentylbicyclo[2.2.2]octane (1.2 g, 80 per cent).

Provenance & Evidence