Hydrochloric Acid → 4-Penten-2-ol p-toluenesulfonate

Participants

Reaction Conditions

Reaction Steps

Under a nitrogen atmosphere, p-toluenesulfonyl chloride (16.92 g, 88.75 mmol) was added to a cold (2° C.), stirring solution of 4-penten-2-ol (7.28 g, 84.52 mmol) in pyridine (60 mL). The solution was stirred at 2-5° C. for 2 h and allowed to warm to ambient temperature over several hours. The mixture, containing white solids, was poured into cold 3M HCl solution (250 mL) and extracted with CHCl3 (4×75 mL). The combined CHCl3 extracts were washed with 3M HCl solution (4×100 mL), saturated NaCl solution (2×50 mL), dried (Na2SO4), filtered, concentrated on a rotary evaporator, and further dried under high vacuum to afford 17.38 g (85.6%) of a light-amber oil.

Provenance & Evidence