Formaldehyde → HCID 13539135, compound

Participants

Reaction Steps

A mixture of 89.0 gm (1.0 mole) N-methylglycine, 60.0 gm (2.0 mole) paraformaldehyde and 144 gm (1.0 mole) dimethyl maleate in 1 L of benzene were heated to reflux with constant water removal for about 5 hours. The reaction mixture was cooled to ambient and allowed to stand over night. The solution was decanted from the solid and the solid was washed with diethyl ether. The combined organic phases were extracted with 10% hydrochloric acid and then this aqueous phase was made basic with concentrated ammonium hydroxide. The now basic aqueous phase was extracted with dichloromethane and the organic extracts were then dried over sodium sulfate and concentrated in vacuo to give a yellow liquid. This material was fractionated through a Vigreaux column to give 74.25 gm of the desired compound, b.p.=119°-123° C. (8 mm Hg).

Provenance & Evidence