Diethyl Ether → 4-Methoxybenzofuran-3(2H)-one

Participants

Reaction Steps

These compounds were prepared from 3-methoxyphenol (1) (6 ml, 55 mmol), ZnCl2 (8.2 g, 60 mmol), and chloroacetonitrile (4.2 g, 66 mmol) in dry ether (100 ml). Purification of the crude product by column chromatography (eluent: CH2Cl2/MeOH: 99/1) gave (2) (1.147 g, 13%), a single compound by HPLC (98% pure, recrystallized from EtOH). 1H-NMR (Acetone-d6, 400 MHz): (7.45 (1 H, d); 6.64 (2 H, m); 4.62 (s, 2 H); 3.95 (s, 3 H) and the more polar compound (3) (1.48 g, 17%). HPLC (84% purity). 1H-NMR (Acetone -d6): δ (400 MHz): values corresponded to previous synthesis of (3).

Provenance & Evidence