Formaldehyde → 1-(Hydroxymethyl)piperidine-2,6-dione

Participants

Reaction Conditions

Reaction Steps

Glutarimide (27 g) and a 35% formaldehyde solution (20 ml) were added to water (40 ml), and heated at about 100° C. for 1 hour over an oil bath. The water was completely distilled away from the reaction mixture using a rotary evaporator. Thus, a crude product of N-methylolglutarimide was obtained. This product was added to 200 ml of benzene without purification, and the resulting solution was heated together with phosphorus tribromide (7.5 ml) under reflux for 1 hour. Thereto, water was added and thereby the benzene layer was separated. The crude product obtained by distilling the benzene away from the benzene layer was recrystallized from an ethyl acetate/n-hexane mixture to yield about 25 g of the desired compound. Melting Point: 165° C.

Provenance & Evidence