Malonic Acid → (2E)-3-(2-Fluoro-5-methoxyphenyl)prop-2-enoic acid

Participants

Reaction Steps

A solution of 2-fluoro-5-methoxybenzaldehyde (10.00 g, 64.9 mmol), malonic acid (13.4 g, 128.8 mmol), piperidine (2.00 mL) and pyridine (100 mL) was heated to 110° C. for 2 h. After this time the solvent was removed in vacuo and the residue taken up in ethyl acetate and washed with aqueous hydrochloric acid (2N, 100 mL). The organic solvent was dried (MgSO4) and the solvent evaporated in vacuo. The solid was recrystallised from hot etahanol to give a white solid (12.2 g, 95%); δH (300 MHz, DMSO) 7.60 (1H, d, J 7 Hz, CH═C), 7.31–7.28 (1H, m, Ar), 7.20 (1H, t, Ar), 7.07–6.97 (1H, m, Ar), 6.62 (1H, d, J 8 Hz, CH═CH), 3.80 (3H, s, OCH3).

Provenance & Evidence