Oleyl alcohol (CAS NO.: ) could be produced through many synthetic methods.

In a 5-l. round-bottomed flask fitted with a large-bore reflux condenser are placed 200 g. (230 ml., 0.65 mole) of ethyl oleate and 1.5 l. of absolute ethanol. Through the reflux condenser is added 80 g. (3.5 gram atoms) of sodium rapidly enough to keep up a vigorous reaction. The flask is shaken occasionally. After the initial reaction has subsided, about 200 ml. more of absolute ethanol is added, and the mixture is heated on a steam bath until all the sodium has reacted. Then 500 ml. of water is added, and the mixture is refluxed for 1 hour to saponify the unreacted ester. The mixture is cooled, and 1.2 l. of water is added. The unsaponifiable fraction is extracted with ether, and the extracts are washed with 1% potassium hydroxide solution and then with water till free of alkali when tested externally with phenolphthalein. The ether extract is dried over sodium sulfate, the ether removed by distillation, and the residue disstilled through an efficient column. A yield of 84–89 g. (49–51%), b.p. 150–152°/1 mm., is obtained.

Fifty grams of the crude oleyl alcohol is crystallized from 400 ml. of acetone at -20° to -25° in a jacketed sintered-glass funnel. The residue, amounting to about 25 g., is then recrystallized from 250 ml. of acetone at -5° to remove saturated alcohols. The oleyl alcohol in the filtrate is recrystallized at -60° to -65°and then distilled from a 25-ml. flask with a thermometer well and a low side arm. The yield is 13–16 g., b.p. 148–150°/less than 1 mm.; n_D25 1.4590.