Butyl bromide → 3-(n-butylamino)phenol

HRID 276088Notes

Reaction equation

HRID 276088 reaction equation
[CH2:1](Br)[CH2:2][CH2:3][CH3:4].C([O-])(O)=O.[Na+].[NH2:11][C:12]1[CH:13]=[C:14]([OH:18])[CH:15]=[CH:16][CH:17]=1>CO>[CH2:1]([NH:11][C:12]1[CH:13]=[C:14]([OH:18])[CH:15]=[CH:16][CH:17]=1)[CH2:2][CH2:3][CH3:4]

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

0.11 mol of n-butyl bromide and 0.1 mol of NaHCO3 are added to 0.1 mol of m-aminophenol in 150 ml of methanol and the mixture is refluxed for 5 h. After cooling, the mixture is filtered and the solvent is removed in vacuo. The oil which remains is fractionated in vacuo, to give 3-(n-butyl-amino)phenol in a yield of 57%; b.p. 110° C. (6·10−5 torr), m.p. 35° C.

Workup

  1. temperaturethe mixture is refluxed for 5 h
  2. temperatureAfter cooling
  3. filtrationthe mixture is filtered
  4. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-8e9ec7a86fcd469fbfb356b872afa383
Source dataset
uspto-grants-2002_03
Patent number
US06353059B2

Reaction notes

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