Dioctadecylamine → [2-(Dioctadecylamino)-2-oxoethoxy]acetic acid

Participants

Reaction Steps

A solution of dioctadecylamine (2.0 g, 3.8 mmol) and diglycolic anhydride (0.44 g, 3.8 mmol) was refluxed in toluene (50 mL) for 48 h. The solvent was then evaporated and the crude product recrystallized form CHCl3 to give (C18H37)2NCOCH2OCH2COOH as a white solid (2.12 g, 87%), mp 80–81° C. 1H-NMR (300 MHz, δ, CDCl3): 0.87 (6H, t, J=6.9 Hz), 1.25 (64H, m), 1.55 (4H, bs), 3.07 (2H, t, J=7.8 Hz), 3.34 (2H, t, J=7.8 Hz), 4.21 (2H, s), 4.38 (2H, s). 13C-NMR (75 MHz, δ, CDCl3): 14.2, 22.8, 26.9, 27.0, 27.5, 28.7, 29.4, 29.5, 29.6, 29.7, 29.8, 32.0, 47.0, 71.4, 73.2, 171.0, 172.2. IR (KBr, cm−1): 1748 (CO), 1602 (CO).

Provenance & Evidence