Hydrogen Bromide → 4,5-Dinitrobenzene-1,2-diol

HRID 346401Notes

Reaction equation

HRID 346401 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.Br>O>[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 260Hydrogen BromideHCID 2229891,2-Dimethoxy-4,5-dinitrobenzene

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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

Workup

  1. temperatureunder refluxing for 6 hours
  2. extractionThe solution was extracted three times with ethyl acetate
  3. washThe organic layer was washed with a 10% sodium hydrogencarbonate
  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-882ae4136e174d48a2245dc5dedf0898
Source dataset
uspto-grants-1991_10
Patent number
US05061794

Reaction notes

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