Acetic Acid → (R)-1-cyclohexyl-1-hydroxy-1-phenyl-2-propanone

Participants

Reaction Steps

To a mixture of 315 ml of 1.4M CH3Li (0.44 mole) in ether and 750 ml of THF at room temperature was added a solution of 26 g (0.11 mole) of (R)-cyclohexylmandelic acid, prepared by the method of R. B. Barlow, F. M. Franks, and J. D. M. Pearson, J. Med. Chem., 16, 439 (1973), in THF. Following the addition, the mixture was stirred at room temperature for 3.5 hours and then brought to reflux for 3 hours. The mixture was cooled and then added dropwise to a mixture of 300 ml of glacial acetic acid and 700 ml of water. This mixture was extracted with ether, the organic layer was separated, washed with water and saturated aqueous sodium bicarbonate, dried, and the solvent removed. The mixture was distilled to give 20 g of clear oil (bp 120° C., 0.1 mm Hg), NMR (chloroform-d) δ7.5(m, 5H), 4.5(S, 1H), 2.4(t, 1H), 2.0(s, 3H), 1.9-1.0(m, 10H).

Provenance & Evidence