4-Nitrophenol → 1-(3-Chloropropoxy)-4-nitrobenzene

HRID 502744Notes

Reaction equation

HRID 502744 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1)([O-:3])=[O:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:18][CH2:19][CH2:20][Cl:21]>C(#N)C>[Cl:21][CH2:20][CH2:19][CH2:18][O:10][C:7]1[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 9804-NitrophenolHCID 80061-Bromo-3-chloropropaneHCID 11430Potassium Carbonate

Product 1

HCID 118446171-(3-Chloropropoxy)-4-nitrobenzene

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 4-Nitrophenol (10 g, 72 mmol) dissolved in acetonitrile (100 ml was charged with potassium carbonate (24.9 g, 180 mmol) and 1-bromo-3-chloropropane (113.2 g, 720 mmol). The mixture was heated and stirred at reflux overnight. The reaction was cooled to room temperature, the solids filtered off and the solvent evaporated under reduced pressure to give the title compound.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux overnight
  3. filtrationthe solids filtered off
  4. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-d27afbcb5608412bb7d27f237be4517c
Source dataset
uspto-grants-2010_08
Patent number
US07776869B2

Reaction notes

Loading…