Hydrochloric Acid → 19082-37-2

Participants

Reaction Steps

To an ice-cold solution of 3.0M phenylmagnesium bromide (100 mL, 300 mmol) under argon atmosphere was added dropwise pent-4-yn-1-ol (10 g, 120 mmol) in diethyl ether (20 mL). After stirring for 3 hours the solution was slowly added to an ice-cold solution of dilute ammonium chloride. 6N Hydrochloric acid was added to break up the gel and the layers were separated. The aqueous extract was washed with diethyl ether (3×50 mL) and the combined organic extracts were washed with brine and dried (MgSO4). The solvent was removed by rotary evaporation under reduced pressure to give 17 g of the crude product which was Kugelrohr distilled to afford 11.1 g (58%) of the purified product. 1H NMR (CDCl3) δ: 1.82-1.95 (m, 2H), 1.98 (t, 1H), 2.20-2.35 (m, 2H), 2.40 (s, 1H), 4.80-4.85 (m, 1H), 7.30-7.38 (m, 5H) ppm.

Provenance & Evidence