4-Toluenesulfonyl chloride → p-Toluenesulfonic acid 1-butyn-3-yl ester

Participants

Reaction Steps

To a solution of tosyl chloride (0.5 mole) and commercial 3-butyn-2-ol (0.4 mole; 40-50% aqueous solution) in ether (350 ml), potassium hydroxide (2.5 moles) is slowly added over a period of 15-30 minutes. The temperature is maintained at 0°-5° C. for the entire period and the reaction mixture is allowed to stand for 90 minutes. When the reaction is complete, the ether phase is washed and dried. Removal of the ether, in vacuo, yields crude 2-tosyloxy-3-butyne.

Provenance & Evidence