Formaldehyde → 3-Phenyloxazolidine

Participants

Reaction Steps

3POX A 500 mL 3-neck flask was equipped with a magnetic stirrer, a reflux condenser, an addition funnel, and a heating mantle with power supply. The flask was charged with 137.17 g (1.0 mole) of N-phenylethanolamine (NPEA) and 25 g of methanol. The addition funnel was charged with 55.20 g of Formcel® (1.01 moles of formaldehyde). The NPEA solution was stirred at room temperature under a blanket of nitrogen, and the Formcel® was added over a period of 1.25 hours. After completing the addition, the reaction mixture was stirred at room temperature overnight. The bulk of the solvent was removed from the reaction mixture by rotary evaporation. Toluene was added to remove water as an azeotrope. The yield of 3POX was 144.54 g (97%) as a clear, amber oil. Product structure was confirmed by NMR and GC/MS analyses.

Provenance & Evidence