Diethyl Oxalate → 4-(2-Hydroxyethyl)morpholine-2,3-dione

Participants

Reaction Conditions

Reaction Steps

A 4(2-hydroxyethyl)morpholine-2,3-dione was prepared by charging 125 g diethyl oxalate and 80 g n-butanol into a suitable reaction vessel and heated to 22° C. under nitrogen blanket. A mixture of 89.9 g diethanolamine and 72 g n-butanol was slowly charged into the reaction vessel while maintaining the reaction mixture below 50° C. After stirring for 30 minutes, the reaction mixture was refluxed for one hour and then allowed to stand at room temperature for 16 hours. The product was collected by filtration and the solid was washed twice with diethyl ether and dried under nitrogen to give 100 g (73.4% yield) of white crystals with 83.3° C.-84.4° C. melting point. IR (Nujol mull) 1759 (ester carbonyl), 1684 (amide carbonyl) cm−1. 1H NMR (500 MHz, acetone-d6) δ 4.592 (approx. triplet, 2H, J=5.0 Hz, ring CH2O), 3.903 (approx. triplet, 2H, J=5.0 Hz, ring CH2N), 3.767 (t, 2H, J=5.5 Hz, CH2OH), 3.597 (t, 2H, J=5.5 Hz, chain CH2N). 13C NMR (500 MHz, D2O) δ158.514 (ester C═O), 155.338 (amide C═O), 67.036 (ring CH2O), 60.399 (CH2OH), 51.034 (ring CH2N), 47.600 (chain CH2N).

Provenance & Evidence