Malonic Acid → 3-Amino-3-(3,4-dimethoxyphenyl)propanoic acid

Participants

Reaction Steps

A stirred suspension of 3,4-dimethoxybenzaldehyde (131 grams, 788 mmol) and ammonium acetate (121.5 grams, 1576 mmol) in ethanol (95%, 400 mL) was heated to 45°-50° C. resulting in an orange solution. To this solution was added malonic acid (82.0 grams, 788 mmol) and the solution was refluxed overnight. A white solid precipitated on heating, the slurry was allowed to cool to room temperature and was filtered. The solid was washed with ethanol, air dried, and dried in vacuo (60° C.,<1 mm) to afford 3-amino-3-(3',4'-dimethoxyphenyl)propionic acid as a white solid, (100.14 grams, 56% yield), no further purification was carded out: mp 208.0°-210.0° C.; 1H NMR (D2 O/NaOD/TSP)δ7.08-6.91 (m, 3H), 4.22 (t, J=7 Hz, 1H), 3.87 (s, 3H), 3.83 (s, 3H), 2.55 (dd, J=2, 7Hz, 2H); 13C NMR(D2 O/NaOD/TSP)δ182.9, 150.8, 149.8, 140.7, 121.6, 114.6, 112.8, 58.6, 55.4, 49.8.

Provenance & Evidence