Sodium Hydroxide → 9-Octadecyn-1-ol

Participants

Reaction Conditions

Reaction Steps

Oleyl alcohol (9.80 g, 36.5 mmoles, Sigma) was placed in a 25 ml 3-neck roundbottom flask equipped with a thermometer, an overhead mechanical stirrer, and a reflux condenser. The contents of the flask were cooled to 15° C. and bromine (5.83 g, 36.5 mmole) was added slowly with stirring at such a rate as to keep the reaction temperature below 30° C. After addition of the bromine, the reaction was stirred at room temperature for 10 minutes. Polyethylene glycol 300 (1.0 g, Fluka) was added followed by powdered sodium hydroxide (3.65 g, 91.3 mmoles). A large exotherm was noted which brought the reaction temperature to 150° C. The reaction was stirred vigorously with heating to maintain a temperature of 125° C. for 2.5 hours. The reaction was cooled and filtered to remove the solid sodium bromide. The filtered salts were washed with 25 ml of hexanes and the solvent removed. The crude product was kugelrohr distilled (ca. 200° C./ 0.20 torr) to yield 9-octadecyn-l-ol (7.89 g, 81% yield) as a clear colorless liquid which solidified upon standing. 1H NMR (CDCl3): 3.61 (q, 2H), 2.12 (m, 4H), 1.02-1.87 (m, 25H), 0.88 (t, 3H) 13C NMR(CDCl3): 79.94, 79.84, 62.33, 32.48, 31.65, 29.19, 29.04, 28.96, 28.66, 28.61, 25.58, 22.45, 18.52, 13.84.

Provenance & Evidence