Glycolic Acid → N,N'-(1,6-hexylene)-bis[2-hydroxyundecylamine] diglycolate

Reaktionsgleichung

[CH2:1]([NH:20][CH2:21][CH:22]([OH:32])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][NH:7][CH2:8][CH:9]([OH:19])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[C:33]([OH:37])(=[O:36])[CH2:34][OH:35].C[OH:39]>>[C:33]([OH:37])(=[O:36])[CH2:34][O:35][CH2:23][C:22]([OH:32])=[O:39].[CH2:1]([NH:20][CH2:21][CH:22]([OH:32])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][NH:7][CH2:8][CH:9]([OH:19])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Komponenten

Edukt 3

HCID 757Glycolic Acid

HCID 887Methanol

HCID 213323471,6-Hexylene-bis[2-hydroxyundecylamine]

Produkt 1

HCID 86734722N,N'-(1,6-hexylene)-bis[2-hydroxyundecylamine] diglycolate

Versuchsvorschrift

A solution of N,N'-(1,6-hexylene-bis[2-hydroxyundecylamine] (5 g.), glycolic acid (1.66 g.) and methanol was heated until the solids dissolved, then evaporated to dryness. Recrystallization of the solid from acetone afforded N,N'-(1,6-hexylene)-bis[2-hydroxyundecylamine] diglycolate (4.6 g., m.p. 88.2°-94.6° C.). In a similar manner using acetic acid and lactic acid instead of glycolic acid there were obtained, respectively, N,N'-(1,6-hexylene)-bis[2-hydroxyundecylamine] diacetate (m.p. 113°-120.6° C.) and N,N'-(1,6-hexylene)-bis[2-hydroxyundecylamine] dilactate (m.p. 102.0°-104.0° C.).