Ethanolamine → benzyl N-(2-hydroxyethyl)carbamate

Participants

Reaction Conditions

Reaction Steps

Benzylchloroformate (44.95 kg, 263.5 mol, 1.0 eq.) was added over a 2 hour period at room temperature to a solution of ethanolamine (16.1 kg, 263.5 mol, 1.0 eq.) in water (34 gal, 128.7 L). After stirring for 30 minutes, this was added to a cold (5-10° C.) solution of NaHCO3 (33.2 kg, 395.25 mol, 1.5 eq) in H2O (330 L) over a 30 min period and then allowed to stir at room temperature overnight. Ethyl acetate (22 gal, 83.3 L) was added, the layers separated, and the aqueous layer extracted again with ethyl acetate (22 gal., 83.3 L). The combined organic extracts were concentrated under vacuum to a volume of 10 gal (37.9 L), and the remainder displaced with isopropyl ether. The resulting slurry was stirred and cooled to 10° C. for 2 hours, then filtered. The solids were washed with isopropyl ether and vacuum dried to give the title compound (39.1 kg, 71.1%). mp 61-63° C. NMR (300 MHz, d6-DMSO): δ=7.50-7.37 (m, 5H), 7.37-7.16 (m, 1H), 5.05 (s, 2H), 4.70-4.63 (m, 1H), 3.46-3.37 (m, 2H), 3.13-3.03 (m, 2H).

Provenance & Evidence