Water → Cyclohexanepentanol

Participants

Reaction Conditions

Reaction Steps

Under nitrogen atmosphere, at 0° C., to a stirring mixture of 2M LiAlH4 (13.04 mL, 26.08 mmol) solution in Et2O in dry Et2O (67 mL), 5-cyclohexylpentanoic acid (1.2 g, 6.52 mmol) in dry Et2O (2 mL) was added dropwise. The mixture was left to react at rt for 4 h, then upon full conversion of the starting material, at 0° C., H2O (13.04 mL), 3M KOH (13.04 mL) solution and H2O (43.65 mL) were very slowly added. The mixture was stirred for 1 h at 0° C., filtered to remove the solid residue, and the remaining organic phase dried over Na2SO4. The organic solution was again filtered and concentrated to dryness affording the title compound (0.98 g, 88%) as a colorless oil. 1H NMR (DMSO-d6): δ 0.77-0.93 (m, 2H), 1.06-1.34 (m, 10H), 1.35-1.47 (m, 2H), 1.56-1.76 (m, 5H), 3.37 (t, J=6.6 Hz, 2H).

Provenance & Evidence