1-Bromooctadecane → 3-Hydroxy-2-methoxypropyl octadecylcarbamate

Participants

Reaction Conditions

Reaction Steps

A suspension of 2.12 g (20 mmol) of 2-methoxy-1,3-propanediol 7.99 g (24 mmol) of octadecyl bromide, 2.43 g (30 mmol) of potassium cyanate and 1.29 g (4 mmol) of tetrabutyl ammonium bromide in 100 ml of dry acetonitrile was refluxed with stirring, at 100° C. for 24 hours. The resultant mixture was then diluted with hot methylene chloride, filtered and the filtrate concentrated in vacuo. The crude product was then purified by flash silica gel chromatography employing a mixture of petroleum ether and ethyl acetate in a 4:1 ratio as the eluent to yield the title compound as a solid, m.p. 56°-58° C.

Provenance & Evidence