4-Nitrophenol → Nitrobenzene

HRID 1858207Notes

Reaction equation

HRID 1858207 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7](O)=[CH:6][CH:5]=1)([O-:3])=[O:2].[OH-].[Na+].C(=O)([O-])[O-].[K+].[K+].Cl.CN(CCCl)C>C1(C)C(C)=CC=CC=1.O>[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

7

Reactant 4

HCID 9804-NitrophenolHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 11636816N,N-Dimethylaminoethyl chloride hydrochloride

Product 1

HCID 7416Nitrobenzene

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 7237O-XyleneSolvent

Procedure

A suspension of 5 g (36 mmol) of 4-nitrophenol in 250 ml of xylene was treated with a solution of 1.63 g (41 mmol) of sodium hydroxide in 20 ml of water and the mixture was stirred at room temperature for 30 minutes. The mixture was then treated with 7.5 g (54 mmol) of potassium carbonate and 5.11 g (36 mmol) of dimethylaminoethyl chloride hydrochloride. The mixture was heated at reflux for 2 hours and then for a further 24 hours with azeotropic removal of water. The mixture was filtered while hot and the solid was washed with hot xylene. The combined filtrate and washings were evaporated and the residue was distilled under a high vacuum to give 1.28 g (20%) of 4-[2-dimethylamino)ethoxy]nitrobenzene as an orange colored liquid.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 2 hours
  3. customfor a further 24 hours with azeotropic removal of water
  4. filtrationThe mixture was filtered while hot and the solid
  5. washwas washed with hot xylene
  6. customThe combined filtrate and washings were evaporated
  7. distillationthe residue was distilled under a high vacuum

Sources & evidence

ORD record
ord-b42bdcb3e2134b8888ab2d96c1eb10d0
Source dataset
uspto-grants-2000_11
Patent number
US06150373

Reaction notes

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