3-(Dimethylamino)phenol → 3-Dimethylaminophenyloctyl ether

HRID 129898

Reaction equation

HRID 129898 reaction equation
[CH3:1][N:2]([CH3:10])[C:3]1[CH:4]=[C:5](O)[CH:6]=[CH:7][CH:8]=1.[OH-:11].[Na+].[CH2:13](Br)[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[CH3:1][N:2]([CH3:10])[C:3]1[CH:4]=[C:5]([CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][O:11][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([N:2]([CH3:10])[CH3:1])[CH:4]=2)[CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 3

HCID 74213-(Dimethylamino)phenolHCID 81401-BromooctaneHCID 14798Sodium Hydroxide

Product 1

HCID 541676423-Dimethylaminophenyloctyl ether

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

200 ml of toluene, 54.8 g (0.4 mol) of 3-dimethylaminophenol and 13.58 g (0.04 mol) of tetrabutylammonium hydrogen sulfate are placed in a 750 ml sulfonating flask having an anchor mixer, thermometer, reflux condenser and dropping funnel and at RT 80 g (1.0 mol) 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 g (0.8 mol) of octyl bromide are added in the course 45 minutes. After a subsequent reaction period of 2.5 hours the mixture is cooled and filtered, and the filtrate is washed with 1×70 ml of H2O, dried over MgSO4, filtered and concentrated by evaporation. The crude product is distilled under a high vacuum, yielding 65.5 g of 3-dimethylaminophenyloctyl ether in the form of a colourless liquid having a boiling point of 150°-152 ° C. (0.1 mbar) which no longer has an OH band in the IR spectrum and of which the NMR analysis is in agreement with the sand structure.

Workup

  1. temperaturethermometer, reflux condenser
  2. customAfter a subsequent reaction period of 2.5 hours the mixture
  3. temperatureis cooled
  4. filtrationfiltered
  5. washthe filtrate is washed with 1×70 ml of H2O
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated by evaporation
  9. distillationThe crude product is distilled under a high vacuum

Sources & evidence

ORD record
ord-dc2799b643e844368c9d3d4553261905
Source dataset
uspto-grants-1995_11
Patent number
US05470896

Linked notes

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