Ethylene Oxide → N-(2-Hydroxyethyl)phthalimide

Participants

Reaction Steps

N-2-Hydroxyethyl phthalimide was prepared by allowing 147.2g (1.0 mole) of phthalimide to react in an autoclave with 53.0g (1.20 moles) of ethylene oxide in the presence of 1.47g (1%) of active chromium III tri-2-ethylhexanoate (COT) and 400 ml of methylisobutyl ketone (MiBK) at 160° to 165°C for two hours. On cooling, the N-2-hydroxyethyl phthalimide crystallized and was collected by filtration. A 94.7% yield of the hydroxyethyl imide was obtained. Under identical experimental conditions but in the absence of COT, the starting material was recovered unchanged.

Provenance & Evidence