Ethanolamine → Butyl 12-[2-hydroxy-3-(2-hydroxyethylamino)propoxy]dodecanate

HRID 1099

Reaktionsgleichung

Reaktionsgleichung von HRID 1099
[CH2:1]([CH2:3][NH2:4])[OH:2].C(O)C.[O:8]1[CH2:30][CH:9]1[CH2:10][O:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([O:25][CH2:26][CH2:27][CH2:28][CH3:29])=[O:24]>O>[OH:8][CH:9]([CH2:30][NH:4][CH2:3][CH2:1][OH:2])[CH2:10][O:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([O:25][CH2:26][CH2:27][CH2:28][CH3:29])=[O:24]

Komponenten

5

Edukt 3

HCID 700EthanolamineHCID 702Ethanol2×HCID 19694655Butyl 12-(2,3-epoxypropoxy)-dodecanate

Produkt 1

HCID 19694611Butyl 12-[2-hydroxy-3-(2-hydroxyethylamino)propoxy]dodecanateAusbeute 55,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A 100-ml flask equipped with a stirrer and dropping funnel was charged with 23.7 g (250 mmol) of ethanolamine and 23.7 g of ethanol. While stirring the mixture at 80° C., an ethanol solution of 8.20 g (25 mmol) of butyl 12-(2,3-epoxypropoxy)-dodecanate was added dropwise over 1 hour. After completion of the reaction, water was added to the reaction mixture, followed by extraction with chloroform. The resultant chloroform solution was concentrated under reduced pressure, and the resultant residue was purified by column chromatography on silica gel, thereby obtaining 5.40 g (yield: 55.4%) of the title compound (Ia-15).

Aufarbeitung

  1. customA 100-ml flask equipped with a stirrer
  2. additionwas added to the reaction mixture
  3. extractionfollowed by extraction with chloroform
  4. concentrationThe resultant chloroform solution was concentrated under reduced pressure
  5. customthe resultant residue was purified by column chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-47ed777a87bd4c2eaf51117084ffdcc4
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05723497

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