p-Toluenesulfonic acid → N-(3-hydroxyphenyl)maleimide

Participants

Reaction Steps

A one-liter flask containing 52.8 grams (0.53 mole) of maleic anhydride dissolved in 200 ml of m-xylene was slowly charged with 55.0 grams (0.50 mole) of 3-aminophenol. The reaction temperature was maintained below 50° C. with cooling. Five grams of para-toluenesulfonic acid was then added to the flask and the reactor contents heated to reflux with a pot temperature of 148°-150° C. Water removal was complete after 8 hours of reflux under nitrogen with a Dean-Stark trap. The flask was cooled, xylene decanted, and the remaining product dried under reduced pressure. One hundred two grams of crude product containing N-(3-hydroxyphenyl) maleimide were recovered.

Provenance & Evidence