N-Hydroxyphthalimide → 2-(2-Phenylethoxy)-1H-isoindole-1,3(2H)-dione

Participants

Reaction Steps

N-Hydroxyphthalimide (15.0 g, 92 mmol) and sodium acetate (7.5 g, 92 mmol) were stirred in dimethylsulfoxide (70 ml) at ambient temperature for 3 h. 2-Chloroethylbenzene (12.5 g, 89 mmol) was added and the reaction mixture was heated at reflux for 2 h. After cooling and standing overnight the reaction mixture was filtered and the flitrate was poured onto ice/water (300 ml). The mixture was extracted with dichloromethane (4×100 ml), the combined extracts were dried (MgSO4) and evaporated in vacuo to a residue. Purification by flash chromatography on a silica gel column eluting with heptane/ethyl acetate (1/1) afforded the title compound as a colourless foam (15.7 g, 33%); 1H NMR (DMSO-d6)γ 3.05 (2H, t, --OCH2 --), 4.39 (2H, t, --CH2Ph), 7.20-7.35 (5H, m, Ar-H), 7.85 (4H, s, Ar-H).

Provenance & Evidence