Palmitic Acid → 2-Methyl-3-pentadecylcarbamoylglycerin

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Reaction Steps

In 50 ml of toluene is dissolved 5.13 g of n-hexadecanoic acid, and 5.5 g of diphenylphosphorylazide and 3 ml of triethylamine are added. The mixture is stirred for 2 hours and further refluxed for one hour. After cooling, the mixture is dissolved in 20 ml of dichloromethane and the solution is added to 20 ml of dichloromethane containing 4.2 g of 2-methylglycerin is added dropwise over a period of 30 minutes. Then, the mixture is refluxed for 2 hours, followed by addition of 200 ml of ice-water. The mixture is stirred vigorously. The dichloromethane layer is separated, dried over sodium sulfate and concentrated to dryness. The residue is subjected to chromatography on a silica gel (60 g) column [eluent: ethyl acetate-n-hexane (1:1)] to give 5.25 g (yield: 73%) of 2-methyl-3-pentadecylcarbamoylglycerin as a colorless powder.

Provenance & Evidence