Potassium Hydroxide → 2-(2-Nonylphenoxy)Ethylamine

HRID 518948

Reaktionsgleichung

Reaktionsgleichung von HRID 518948
[O:1]1[CH2:5][CH2:4][NH:3][C:2]1=O.[CH2:7]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1O)[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]C.[OH-].[K+]>>[CH2:9]([C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:2]=1[O:1][CH2:5][CH2:4][NH2:3])[CH2:8][CH2:7][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]

Komponenten

4

Edukt 3

HCID 14797Potassium HydroxideHCID 67296NonylphenolHCID 739492-Oxazolidinone

Produkt 1

HCID 544240572-(2-Nonylphenoxy)Ethylamine

Versuchsvorschrift

To a 250 mL round bottom flask equipped with a thermocouple, heating mantle, nitrogen inlet/outlet, a condenser and a stir bar was added 2-oxazolidinone (6.72 g, 77.2 mmole), 2-nonylphenol (10.0 g, 45.4 mmole), potassium hydroxide (255 mg, 4.5 mmole) and ExxonMobil™ Aromatic 100 solvent (70 mL). The resulting mixture was heated to reflux temperature for 3 h. Reaction progress was monitored by TLC and 1H NMR. The reaction mixture was then cooled, filtered over Celite® and the solvent were evaporated under reduced pressure. The crude material was purified using flash column chromatography to give the amine. 1H NMR (DMSO-d6, 400 MHz) δ 7.26-7.12 (m, 2H), 6.88-6.81 (m, 2H), 3.87 (dd. 2H, J=5.8, 5.8 Hz), 2.86 (dd, 2H, J=5.8, 5.8 Hz), 1.75-0.42 (m, 19H).

Aufarbeitung

  1. customTo a 250 mL round bottom flask equipped with a thermocouple
  2. temperatureheating mantle, nitrogen inlet/outlet, a condenser and a stir bar
  3. temperatureThe resulting mixture was heated
  4. temperatureto reflux temperature for 3 h
  5. customReaction progress
  6. temperatureThe reaction mixture was then cooled
  7. filtrationfiltered over Celite®
  8. customthe solvent were evaporated under reduced pressure
  9. customThe crude material was purified

Quellen und Nachweise

ORD-Eintrag
ord-fdc4e70c492b41c9b2422db411c072a7
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09115237B2

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