Dimethylamine → 2-Methylene-4-phenylbutyric acid

Participants

Reaction Steps

A mixture of 2-phenylethylmalonic acid (1.8 g), 40% aqueous dimethylamine (1.08 ml, 1 eq) and 37% aqueous formaldehyde (0.64 ml, 1 eq) in water (10 ml) was stirred at room temperature overnight. After cooling at 0° C. the solid was filtered off, washed with water and dried. The white solid was heated at 170° C. for 10 minutes and cooled to room temperature. The resulting gum was dissolved in ethyl acetate (20 ml), washed with 10% potassium hydrogen sulphate solution (10 ml), water (2×10 ml), saturated brine (10 ml), dried (MgSO4) and evaporated to give crude 2-methylene-4-phenylbutanoic acid. δH (CDCl3) 2.55-2.90 (4H, m, 2×CH2), 5.65, 6.85 (2H, 2×s, H), 7.25 (5H, m, Ph).

Provenance & Evidence