2,4,6-Tris((dimethylamino)methyl)phenol → 2,4,6-Tris(dimethylaminomethyl)phenyloctyl ether

HRID 129896Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 129896
[CH3:1][N:2]([CH2:4][C:5]1[CH:10]=[C:9]([CH2:11][N:12]([CH3:14])[CH3:13])[CH:8]=[C:7]([CH2:15][N:16]([CH3:18])[CH3:17])[C:6]=1O)[CH3:3].[OH-:20].[Na+].[CH2:22](Br)[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[CH3:1][N:2]([CH2:4][C:5]1[CH:10]=[C:9]([CH2:11][N:12]([CH3:14])[CH3:13])[CH:8]=[C:7]([CH2:15][N:16]([CH3:18])[CH3:17])[C:6]=1[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][O:20][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][C:8]1[C:7]([CH2:15][N:16]([CH3:18])[CH3:17])=[CH:6][C:5]([CH2:4][N:2]([CH3:1])[CH3:3])=[CH:10][C:9]=1[CH2:11][N:12]([CH3:14])[CH3:13])[CH3:3]

Komponenten

6

Edukt 3

HCID 70262,4,6-Tris((dimethylamino)methyl)phenolHCID 81401-BromooctaneHCID 14798Sodium Hydroxide

Produkt 1

HCID 570201012,4,6-Tris(dimethylaminomethyl)phenyloctyl ether

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 94433Tetrabutylammonium hydrogen sulfateKatalysatorHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

106.16 g (0.4 mol) of 2,4,6-tris(dimethylaminomethyl)phenol and 13.58 g (0.04 mol) of tetrabutylammonium hydrogen sulfate are placed in 200 ml of toluene in a 750 ml sulfonating flask having an anchor mixer, thermometer, reflux condenser and dropping funnel and at RT 80 g (1.0 tool) of a 50% aqueous NaOH solution are added dropwise in the course of 30 minutes. The suspension is then stirred for 30 minutes at 80° C. and then at the same temperature 154.5 g (0.8 mol) of octyl bromide are added in the course of 45 minutes. After a subsequent reaction period of 2 hours the mixture is cooled and filtered, and the filtrate is washed once with 30 ml of H20, dried over MgSO4, filtered and concentrated by evaporation, yielding 137.4 g of 2,4,6-tris(dimethylaminomethyl)phenyloctyl ether in the form of a brown, highly viscous liquid which no longer has an 0H band in the IR spectrum and of which the NMR analysis is in agreement with the said structure.

Aufarbeitung

  1. temperaturethermometer, reflux condenser
  2. customAfter a subsequent reaction period of 2 hours the mixture
  3. temperatureis cooled
  4. filtrationfiltered
  5. washthe filtrate is washed once with 30 ml of H20
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated by evaporation

Quellen und Nachweise

ORD-Eintrag
ord-e1273317fe014cfa9c4e06116f9a0071
Quelldatensatz
uspto-grants-1995_11
Patentnummer
US05470896

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