4-Tert-butylcyclohexane-1-carboxylic acid → 4-tert-Butylcyclohexylmethanol

Participants

Reaction Steps

To a cooled (0° C.) solution of 4-tert-butylcyclohexane-carboxylic acid (3.00 g, 16.3 mmoles) in THF (30 mL) is slowly added a THF solution of borane-THF complex (1.0M, 21.2 mL, 21.2 mmoles). The solution is stirred at room temperature for 18 hours, then quenched with 2N HCl solution (30 mL), and extracted with EtOAc. The organic layer is isolated, washed with 1N NaOH, dried over sodium sulfate, and concentrated to yield the title compound as a clear oil. 1H NMR (300 MHz, CDCl3): δ 2.06 (d, 2H), 1.82 (m, 4H), 1.52 (m, 2H), 0.88 (m, 4H), 0.83 (s, 9H).

Provenance & Evidence