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

HRID 1042700Notes

Reaction equation

HRID 1042700 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-92319e21d3234f9a8e4b35e029dc57a6
Source dataset
uspto-grants-2013_10
Patent number
US08557996B2

Reaction notes

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