p-Toluenesulfonic acid → 3-Hexadecyloxybutane-1,2-diol

Participants

Reaction Steps

A mixture of 30 g of [1-(hexadecyloxy)ethyl]oxirane, 0.2 g of p-toluenesulfonic acid and 200 ml of glacial acetic acid was refluxed for 4.5 hours, then the acetic acid was removed. Toluene was added and removed. The residue was dissolved in 225 ml of methanol and 13.44 g of sodium hydroxide in 14 ml of water was added. This mixture was stirred 1/2 hour, the solvent removed and the residue extracted twice with ether. The ether extracts were combined, washed with brine, dried and the solvent removed. The resulting oil was diluted via a Kugelrohr (200° C., 0.5 mm), giving 28.87 g of the desired compound as a white sticky solid.

Provenance & Evidence