Stearyl Alcohol → n-Octadecyl Sorbate

Participants

Reaction Steps

A solution of 0.9 g (6.9 mmol) of sorboyl chloride in 6 mL of THF was added slowly with stirring to a mixture of 1.87 g (6.9 mmol) of n-octadecanol in 10 mL of THF at 40° C. The resulting mixture was refluxed for 16 hours. The solvent was evaporated under reduced pressure and the crude product was purified by column chromatography on silica gel using chloroform as eluent. The appropriate fractions were combined and evaporated to dryness in vacuo to give a white solid product: 1.04 g (42%) yield. TLC (CHCl3)Rf=0.75. 1H NMR (300 MHz) δ 0.89 [3H, t, —(CH3)15CH3)],1.25 [30H, br m, —(CH3)15—], 1.62 [2H, t, —OCH2CH2—], 1.86 [3H, d, CH3CH═], 4.14 [2H, t, —OCH2—], 5.79 [1H, d, OCCH═], 6.19 [2H, m, CH3CH═CH—], 7.22 [1H, m, CH3CH═CH—CH═].

Provenance & Evidence