Carbon Dioxide → HCID 12909166, compound

Participants

Reaction Conditions

Reaction Steps

The compound 4-nitrophenylacetic acid (30.2 g, 0.166 mole) was dissolved in 210 ml (1.7 mole) of 33% aqueous dimethylamine solution and cooled to 10° C. in an ice bath. Immediately to the reaction solution was added dropwise 150 ml of 38% aqueous formaldehyde solution, under a nitrogen atmosphere, while maintaining the temperature between 15°-20° C. When the addition of the formaldehyde was complete, the reaction mixture was stirred for 0.5 hours at 20° C., then for 0.5 hours with warming to 60° C. (evolving carbon dioxide), and then for 10 hours at room temperature. The light yellow oil, which separated from solution, was taken up in 3×30 ml portions of chloroform. The chloroform layer was extracted with 3×30 ml portions of 3N hydrochloric acid. Upon neutralization with saturated potassium bicarbonate solution an oily layer was separated, extracted with 3×30 ml portions of chloroform, washed with an equal volume of saturated sodium chloride solution, and dried over anhydrous Na2SO4. Evaporation of the chloroform provided 31.5 g (93%) of crude α-(N,N-dimethylaminomethyl)-p-nitrostyrene.

Provenance & Evidence