Benzyl Alcohol → Benzyl 16-hydroxyhexadecanoate

Participants

Reaction Steps

This compound was prepared from 16-hydroxyhexadecanoic acid (2.45 g; 9.0 mmol), benzyl alcohol (4.9 g; 45 mmol), and p-toluenesulphonic acid (100 mg) in toluene (100 mL) using Procedure B. 2.82 g crude product that was a 1:1 mixture of the expected product and the ester between two molecules of 16-hydroxyhexadecanoic acid was obtained. A solution of NaH (ca. 100 mg) (previously washed three times with dry hexane) in benzyl alcohol (10 g) was added to the crude product and the mixture was stirred at 100° C. (bath temperature) under argon for 3 h. After cooling to ambient temperature, the mixture was diluted with dichloromethane (75 mL) and washed with 10% aqueous citric acid solution (1×10 mL) and dried (Na2SO4). After filtration and evaporation, the residue was vacuum dried at 50° C. (bath temperature) and 0.014 mm Hg using a Kugelrohr apparatus. 2.56 g (76%) product was obtained (white solid). Proton NMR indicated that ca. 10% of the dimer ester remained.

Provenance & Evidence