Formaldehyde → Ethyl alpha-(phenethyl)acrylate

Participants

Reaction Conditions

Reaction Steps

To the 2-ethoxycarbonyl-3-phenylbutanoic acid (3.5 g) is added diethylamine (1.53 mL, 1 eq) and 30% formaldehyde (1.78 mL) at 0° C. The mixture is stirred overnight at a temperature of about 20° C. and is then taken up with diethyl ether (100 mL). The organic phase is separated after settling takes place, washed with 10% aqueous citric acid solution (40 mL) and finally dried over sodium sulphate. After filtering and concentrating to dryness, 2.2 g of ethyl 2-(phenylethyl)acrylate is obtained in a 71% yield in the form of a yellow oil, having the following characteristics: Rf =0.86 [methylene chloride/methanol (9:1 by volume)].

Provenance & Evidence