3-Methylcyclohexanecarboxylic acid → (3-Methylcyclohexyl)methanol

Participants

Reaction Steps

To a boran-methyl sulfide complex (1.7 ml, 0.028 mole) in 7 ml tetrahydrofuran, at 0° C., was added dropwise 2 g of 3-methylcyclohexanecarboxylic acid (0.014 mole) in 7 ml tetrahydrofuran. Stirring was continued for one hour. The reaction mixture was diluted with ether and washed with 1N aqueous sodium hydroxide and then with brine. Concentration and distillation gave 1.34 g of the title compound The NMR spectrum showed absorption at 0.54-0.74 (m, 1H), 0.90, 0.93 (s, 3H), 1.17-1.53 (m, 3H), 1.65-1.77 (m, 3H) and 3.39-3.52 (m, 2H).

Provenance & Evidence