Palmitoyl chloride → Tert-butyl 3-hexadecanoyloxyoctadecanoate

Participants

Reaction Conditions

Reaction Steps

To tert-butyl 3-hydroxyoctadecanoate (120 g) in pyridine (500 ml) was added palmitoyl chloride (120 g) at 0° C. The mixture was stirred at 0° C. for 5 hours and then allowed to stand over-night at room temperature. Pyridine was removed under reduced pressure and the residue was poured into water. The resulting mixture was stirred at ambient temperature for 2 hours, acidified with 1N HCl, extracted with ethyl acetate, and washed with water. Evaporation of the solvent gave a residue which was purified by silica gel column chromatography (30% CH2Cl2 --CCl4) to afford tert-butyl 3-hexadecanoyloxyoctadecanoate (160 g) as an oil.

Provenance & Evidence