Hydrochloric Acid → 1-cyclohexyl-1-phenylprop-2-yn-1-ol

Participants

Reaction Conditions

Reaction Steps

Lithium acetylide (47.84 g, 0.52 mole) was added to 70 ml of THF. The solution was cooled to 0° C. and a solution of cyclohexyl phenyl ketone in 100 ml of THF was added over a period of 15 minutes with stirring. The solution was allowed to warm to room temperature and stirred for 16 hours. The solution was then cooled to 0° C. and 50 ml of a 5N HCl was added. The solution was then warmed to room temperature and 200 ml of water was added. The solution was transferred to a separatory funnel and washed with ether. The ether washes were combined and dried. Upon removal of the ether under vacuum and vacuum distillation of the crude product a pale yellow oil was isolated (60.33 g, 82.9%): bp 111°-4° C. (0.8 mm), NMR (CDCl3) δ7.7-7.2(m, 5H), 2.6(s, 1H), 2.3(s, 1H), 2.1-0.9(m, 11H). IR (neat) 3433, 3304, 2111, 1448, 1016 cm-1.

Provenance & Evidence