Ethanolamine → 1-(2-Hydroxyethylamino)-2,16-hexadecanediol

Reaction equation

[CH2:1]([CH2:3][NH2:4])[OH:2].N#N.[O:7]1[CH:9]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][OH:24])[CH2:8]1>C(O)C>[OH:2][CH2:1][CH2:3][NH:4][CH2:8][CH:9]([OH:7])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][OH:24]

Participants

Procedure

A 50-ml two-necked flask equipped with a stirrer, dropping funnel and N2 inlet tube was charged with 4.14 g (68 mmol) of ethanolamine and 0.8 g of ethanol. While heating and stirring the mixture at 80° C. in an N2 atmosphere, an ethanol solution of 0.87 g (3.4 mmol) of 1,2-epoxy-16-hexadecanol was added dropwise over 1.5 hours. The resultant mixture was stirred further for 2 hours at 80° C. After completion of the reaction, ethanol and excess ethanolamine were distilled off under reduced pressure, and the resultant residue was purified by flash column chromatography on silica gel, thereby obtaining 0.72 g (yield: 68%) of the title compound (IId-1).