4-(3-Chloropropoxy)-3-methoxybenzeneacetic acid ethyl ester → 4-[3-(1,3-Dihydro-1,3-dioxo-2H-isoindol-2-yl)propoxy]-3-methoxybenzeneacetic acid ethyl ester

Participants

Reaction Steps

A mixture of 40.5 g (0.141 mole) of 4-(3-chloropropoxy)-3-methoxybenzeneacetic acid ethyl ester and 27.2 g (0.144 mole) of potassium phthalimide (98%, Aldrich) in 300 mL of dimethylformamide was stirred and heated at reflux for 5 h, then was stirred at ambient temperature overnight. The solvent was evaporated under reduced pressure to give 52.3 g (93%) of a gummy residue which solidified upon standing. An analytical sample, mp 70°-72° C., was prepared from ethyl ether-petroleum ether (30°-60° C.) as a white solid.

Provenance & Evidence