Reaction #452414

ord-1d3d42166217481ba4169187abe09eeb

Reaction equation

CCCCBr
n-butyl bromide
O=C([O-])O.[Na+]
NaHCO3
Nc1cccc(O)c1
m-aminophenol
CCCCNc1cccc(O)c1
3-(n-butylamino)phenol
Yield 57.0%

Solvents

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Temperaturethe mixture is refluxed for 5 h
  2. 2
    TemperatureAfter cooling
  3. 3
    Filtrationit is filtered
  4. 4
    Otherthe solvent is removed in vacuo

Procedure

0.11 mol of n-butyl bromide and 0.1 mol 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, it is filtered and the solvent is removed in vacuo. The oil which remains is fractionated in vacuo, to give 3-(n-butylamino)phenol.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US06126867uspto-grants-2000_10