Thionyl bromide → 2-Bromo-1,3-dioctadecyloxypropane

Participants

Reaction Conditions

Reaction Steps

To a solution of 11.0 g of 1,3-dioctadecyloxy-2-propanol in 400 ml of dry dimethylformamide 20 g of thionyl bromide were added dropwise, while stirring well and boiling, after which the reaction mixture was heated at 100° C for 5 hours. After cooling down said mixture was slowly poured out into 400 ml of 5% sodium bicarbonate solution. The aqueous solution was extracted with 4 × 150 ml of hexane, after which the hexane extract was consecutively washed with water, 5% sodium bicarbonate solution, and water. After drying on sodium sulphate 0 aq the solvent was removed under vacuum. The resulting coarse product was purified by means of column chromatography. After evaporation and drying in vacuum (P = 0.001 mm Hg, t = 40° C) 8 gram were obtained, melting point 47.9° - 48.7° C.

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