Cetyl Alcohol → Hexadecanal

Participants

Reaction Steps

A solution comprising 10 g (85 mmole) of 1-hexadecanol in 100 ml of methylene chloride was added to a mixture comprising 10 g (139 mmole) of pyridinium chlorochromate, 30 g of celite and 12.0 g (146 mmole) of anhydrous sodium acetate in 400 ml of methylene chloride in a dropwise fashion. Following addition, the reaction mixture was stirred at room temperature for three hours then 300 ml of diethyl ether was added. The reaction mixture was filtered and a precipitate was collected and washed with diethyl ether until clear. The solvent was removed under reduced pressure and the residue passed through Florisil with diethyl ether as the eluent. The solvent was removed under reduced pressure and the residue purified by flash chromatography on silica (230 to 400 mesh) with hexanes and ethyl acetate at a ratio of approximately 39 to 1. The synthesis yielded hexadecanal having a mass of approximately 17.5 g and of approximately 88.4% purity. Hexadecanal is a white wax having a melting point of approximately 33°-34 C. The 1H NMR spectrum of the compound at 300 MHz using CDCl3 comprised the following peaks: δ 0.892 (3H, t, J=6.5Hz), 1.267 (24H, bs), 1.61 to 1.66 (2H, m), 2.430 (2H, dt, J=1.7 and 7.3 Hz), and 9.776 (1H, s).

Provenance & Evidence