Hydrochloric Acid → Adamantane-1,4-diol

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Reaction Steps

Sodium borohydride (3.00 g) is added in three equal portions to a solution of 5-hydroxy-adamantan-2-one (5.00 g) in methanol (100 mL) chilled in an ice bath. The mixture is stirred in the cooling bath for 1 h and at room temperature overnight. 1 M hydrochloric acid is added and the resulting mixture is stirred for 0.5 h. The mixture is concentrated, water is then added to the residue, and the resulting mixture is extracted with ethyl acetate. The combined extract is washed with brine, dried (MgSO4), and concentrated to give the title compound as a mixture of diastereomers (ca. 1:1). Yield: 3.20 g (63% of theory); Mass spectrum (ESI+): m/z=186 [M+NH4]+.

Provenance & Evidence