Triethylamine → Oleyl methane sulfonate

Participants

Reaction Steps

Oleyl alcohol, also called cis 9 octadecen-1-ol, (100 g, 0.37M) was dissolved in DCM, dichloromethane and cooled to 0° C. Triethylamine (56.5 g, 78 ml, 0.56M, 1.5 equivalents) was added to the solution at this temperature and the mixture was stirred for one hour. Methanesulphonyl chloride (47 g, 31.8 ml, 1.1 equivalents) was then added to the mixture at this temperature and the mixture was stirred at 0° C. for 30 minutes before being allowed to warm to room temperature. The reaction mixture was washed with ice/water, cold 10% hydrochloric acid, cold solution of sodium bicarbonate, water and brine successively, then dried with sodium sulphate. After filtration, the solvent was removed under vacuum to yield and oil which was chilled overnight to yield a solid with a low melting point (yield 126.5 g, 99%).

Provenance & Evidence