Water → 4,5-Dinitrobenzene-1,2-diol

HRID 483364Notes

Reaction equation

HRID 483364 reaction equation
C[O:2][C:3]1[C:8]([O:9]C)=[CH:7][C:6]([N+:11]([O-:13])=[O:12])=[C:5]([N+:14]([O-:16])=[O:15])[CH:4]=1.O>Br>[OH:2][C:3]1[C:8]([OH:9])=[CH:7][C:6]([N+:11]([O-:13])=[O:12])=[C:5]([N+:14]([O-:16])=[O:15])[CH:4]=1

Participants

4

Reactant 2

HCID 962WaterHCID 2229891,2-Dimethoxy-4,5-dinitrobenzene

Product 1

HCID 141714294,5-Dinitrobenzene-1,2-diolYield 79.5%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

10 g (44 mmol) of 4,5-dimethoxy-1,2-dinitrobenzene was suspended in 150 ml of 45% hydrobromic acid, and the suspension was refluxed at a boiling point for 6 hours. The reaction solution was allowed to cool to room temperature, and 500 ml of water was added thereto. The mixture was extracted three times with ethyl acetate. The organic layer was washed with a 10% sodium bicarbonate aqueous solution and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. The crystal residue was washed with methylene chloride to obtain 7 g (yield: 79%) of 4,5-dihydroxy1,2-dinitrobenzene.

Workup

  1. temperaturethe suspension was refluxed at a boiling point for 6 hours
  2. extractionThe mixture was extracted three times with ethyl acetate
  3. washThe organic layer was washed with a 10% sodium bicarbonate aqueous solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. washThe crystal residue was washed with methylene chloride

Sources & evidence

ORD record
ord-9f05c8bc582f407aac046856dc43d729
Source dataset
uspto-grants-1993_07
Patent number
US05225406

Reaction notes

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