A rapid stream of dry acetylene is passed into approximately 1 l. of liquid ammonia in a 2-l. three-necked flask equipped with a gas inlet tube and a mechanical stirrer while 23 g. (1 gram atom) of sodium is added over a period of 30 minutes (Note 1) and (Note 2). The flow of acetylene is then reduced (Note 3), and 98 g. (1 mole) of cyclohexanone is added dropwise. When this addition, which requires about an hour, is completed, the reaction mixture is allowed to stand for about 20 hours to permit the evaporation of nearly all the ammonia (Note 4).

The solid residue is decomposed by adding approximately 400 ml. of ice and water, and the resulting mixture is carefully acidified with 50% sulfuric acid (Note 5). The organic layer is dissolved in 100 ml. of ether and washed with 50 ml. of brine. The original aqueous phase and the brine wash are then extracted with two 50-ml. portions of ether. The combined ethereal solutions are dried over anhydrous magnesium sulfate and filtered, and the ether is distilled. The product is then distilled under reduced pressure through a good column (Note 6). The yield of 1-ethynylcyclohexanol is 81–93 g. (65–75%), b.p. 74°/14 mm.; n²⁰D 1.4822 (Note 7).