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

HRID 129895Notes

Reaction equation

HRID 129895 reaction equation
[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][CH3:25]>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[CH2:25][CH2:24][CH2:23][CH2:22][O:20][CH2:4][CH2:5][CH2:6][CH2:7][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]

Participants

6

Reactant 3

HCID 70262,4,6-Tris((dimethylamino)methyl)phenolHCID 8002Butyl bromideHCID 14798Sodium Hydroxide

Product 1

HCID 570895352,4,6-Tris(dimethylaminomethyl)phenylbutyl ether

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

53.1 g (0.2 mol) of 2,4,6-tris(dimethylaminomethyl)phenol and 6.8 g (0.02 mol) of tetrabutylammonium hydrogen sulfate are placed in 100 ml of toluene in a 350 ml sulfonating flask having an anchor mixer, thermometer, reflux condenser and dropping funnel and at RT 40 g (0.5 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 54.8 g (0.4 mol) of butyl bromide are added in the course of 45 minutes. After a subsequent reaction period of 3 hours the mixture is cooled and filtered, and the filtrate is washed once with 30 ml of H2O, dried over MgSO4, filtered and concentrated by evaporation, yielding 48 g of 2,4,6-tris(dimethylaminomethyl)phenylbutyl ether in the form of a brown liquid which no longer has an OH band in the IR spectrum and of which the NMR analysis is in agreement with the said structure.

Workup

  1. temperaturethermometer, reflux condenser
  2. customAfter a subsequent reaction period of 3 hours the mixture
  3. temperatureis cooled
  4. filtrationfiltered
  5. washthe filtrate is washed once with 30 ml of H2O
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-10c63a6c2f0f4313abbd01600518e161
Source dataset
uspto-grants-1995_11
Patent number
US05470896

Reaction notes

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