2-Phenylethanol → Phenethyl (E)-caffeate

Participants

Reaction Steps

A solution of 1.80 g (10.0 mmol) of caffeic acid, 17.9 mL (150 mmol) of β-phenylethyl alcohol and 100 mg of p-toluenesulfonic acid in benzene (100 mL) were stirred overnight at reflux with a Dean Stark trap. Solvent and excess alcohol were removed by distillation and residue purified by silica gel chromatography (petroleum ether/CHCl3). Product was crystallized (ether/petroleum ether) to provide 67H-42-A as snow-white crystals, 1.0 g (35%): mp 128.0° C. 126°-128° C.) (Grunberger, D. et al., Experimentia, (1988) 44:230-2).

Provenance & Evidence