Butyl bromide → 3-(n-butylamino)phenol

HRID 1976761Notes

Reaction equation

HRID 1976761 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.[CH2:9](Br)[CH2:10][CH2:11][CH3:12].C([O-])(O)=O.[Na+]>CO>[CH2:9]([NH:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1)[CH2:10][CH2:11][CH3:12]

Participants

5

Reactant 3

HCID 8002Butyl bromideHCID 115683-AminophenolHCID 516892Sodium Bicarbonate

Product 1

HCID 111266263-(n-butylamino)phenolYield 57%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

One-tenth mol of m-aminophenol in 150 ml methanol is treated with 0.11 mol of n-butyl bromide and 0.1 mol of NaHCO3 and the mixture is heated under reflux for 5 h. After cooling, the reaction mixture is filtered and the solvent removed under reduced pressure. The residual oil is vacuum fractionated to give 3-(n-butylamino)phenol.

Workup

  1. temperaturethe mixture is heated
  2. temperatureunder reflux for 5 h
  3. temperatureAfter cooling
  4. filtrationthe reaction mixture is filtered
  5. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-1fef69f2c82c4c429e9e3ab1bbd91205
Source dataset
uspto-grants-2001_05
Patent number
US06228977B1

Reaction notes

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