Water → 2,6-Dichloro-4-nitrophenol

HRID 1532205Notes

Reaction equation

HRID 1532205 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N+:10]([O-:12])=[O:11])[CH:5]=[C:6]([Cl:9])[C:7]=1Cl.[O-:13]C1C=CC=CC=1.[K+].O>C(O)COCCO>[Cl:1][C:2]1[CH:3]=[C:4]([N+:10]([O-:12])=[O:11])[CH:5]=[C:6]([Cl:9])[C:7]=1[OH:13]

Participants

5

Reactant 3

HCID 962WaterHCID 883653,4,5-TrichloronitrobenzeneHCID 23670670Potassium phenoxide

Product 1

HCID 120662,6-Dichloro-4-nitrophenol

Reagents, catalysts & solvents 1

HCID 8117Diethylene GlycolSolvent

Conditions

Temperature
160 °C

Procedure

3,4,5-Trichloronitrobenzene (14.86 g) is added to a solution of potassium phenoxide (8.66 g) in diethylene glycol (66 mL) and the mixture is heated to 160° C. for approximately 15 hours. The resulting dark brown solution is cooled to room temperature, poured onto 100 mL cold water, and extracted twice with diethyl ether. The pooled organic extracts are washed with water, 10% aqueous sodium hydroxide, and then dried over anhydrous magnesium sulfate. Following removal of the solvent under reduced pressure the resulting oil is distilled in a Kugelrohr apparatus to provide a yellow oil that solidifies on standing. Recrystallization from ethanol-water provides the desired product as a pale yellow solid.

Workup

  1. temperatureThe resulting dark brown solution is cooled to room temperature
  2. extractionextracted twice with diethyl ether
  3. washThe pooled organic extracts are washed with water, 10% aqueous sodium hydroxide
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customremoval of the solvent under reduced pressure the resulting oil
  6. distillationis distilled in a Kugelrohr apparatus
  7. customto provide a yellow oil
  8. customRecrystallization from ethanol-water

Sources & evidence

ORD record
ord-6c044d5748ef44809d37a42686eada59
Source dataset
uspto-grants-2001_03
Patent number
US06201013B1

Reaction notes

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