Catechol → Nitrocatechol

HRID 1195988Notes

Reaction equation

HRID 1195988 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-6ad94b14fda4429a8b99feb0d7dcb86b
Source dataset
uspto-grants-1992_05
Patent number
US05112861

Reaction notes

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