Water → 4-Benzoyloxy-1-octyne

Participants

Reaction Steps

To a stirred solution of 63 g (0.50 moles) of 1-octyn-4-ol (Example 93) in 500 ml of pyridine is added 77 g (0.55 moles) of benzoyl chloride. After stirring for 1.5 hours the mixture is treated with 10 ml of water, allowed to stand for 15 minutes, and concentrated. A solution of the residue in ether is washed successively with ice-cold hydrochloric acid, water, sodium bicarbonate solution, and brine. The solution is dried over magnesium sulfate, filtered through Celite, and concentrated to give an oil, λmax. 3240 (terminal acetylene) and 1730 cm-1 (benzyloxy group).

Provenance & Evidence