Catechol → Nitrocatechol

HRID 1757668Notes

Reaction equation

HRID 1757668 reaction equation
[C:1]1([C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4])[OH:2].[N+:9]([O-])([OH:11])=[O:10]>CCOCC>[N+:9]([C:5]1[CH:6]=[CH:7][CH:8]=[C:1]([OH:2])[C:3]=1[OH:4])([O-:11])=[O:10]

Participants

4

Reactant 2

HCID 289CatecholHCID 944Nitric Acid

Product 1

HCID 4675622Nitrocatechol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution containing 2.5 g of catechol in 125 ml of ether 1.0 ml of conc. nitric acid (d-1.52) was gradually added. The solution was stirred over night at room temperature and washed with water. The solvent was evaporated and the residue was treated with boiling petroleum ether (b.p. 60°-80° C). The insoluble 4-nitrocatechol was filtered and the filtrate concentrated in vacuo. After cooling the 3-nitrocatechol was filtered. Yield 0.85 g (24%), m.p. 82°-85° C.

Workup

  1. additionwas gradually added
  2. washwashed with water
  3. customThe solvent was evaporated
  4. additionthe residue was treated with boiling petroleum ether (b.p. 60°-80° C)
  5. filtrationThe insoluble 4-nitrocatechol was filtered
  6. concentrationthe filtrate concentrated in vacuo
  7. temperatureAfter cooling the 3-nitrocatechol
  8. filtrationwas filtered

Sources & evidence

ORD record
ord-10978cc9259c481ca7e4a42301264be7
Source dataset
uspto-grants-1995_08
Patent number
US05446194

Reaction notes

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