Ethanolamine → 1-(2-Hydroxyethylamino)-3-(12-hydroxyoctadecyloxy)-2-propanol

HRID 1094

Reaction equation

[CH2:1]([CH2:3][NH2:4])[OH:2].[CH2:5]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH:21]([OH:28])[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[CH:6]1[O:8][CH2:7]1>C(O)C>[OH:2][CH2:1][CH2:3][NH:4][CH2:7][CH:6]([OH:8])[CH2:5][O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH:21]([OH:28])[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]

Participants

Conditions

Temperature: 80 °C

Procedure

A 200-ml flask equipped with a stirrer, reflux condenser and dropping funnel was charged with 35.0 g (0.57 mol) of ethanolamine and 35 g of ethanol, and the mixture was heated to 80° C. with stirring in a nitrogen atmosphere. To this mixture, 13.0 g (38 mmol) of 12-hydroxyoctadecyl glycidyl ether were added dropwise over 3 hours. After the resultant mixture was stirred further for 3 hours, it was concentrated under reduced pressure and purified by column chromatography on silica gel, thereby obtaining 11.7 g (yield: 77%) of the title compound (Ia-1).

Workup

customA 200-ml flask equipped with a stirrer
temperaturereflux condenser
concentrationit was concentrated under reduced pressure
custompurified by column chromatography on silica gel

Sources & evidence

ORD record: ord-0aef768b43124d028d286302e483b8f7
Source dataset: uspto-grants-1998_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05723497

Linked notes

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