Catechol → Nitrocatechol

HRID 501523Notes

Reaction equation

HRID 501523 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 of catechol (5 g, 45 mmol) in Et2O (187 mL) cooled to 0° C. was added dropwise fuming HNO3 (2 mL). After addition, the reaction was allowed to stand at rt overnight, and the Et2O was removed by evaporation under reduced pressure. The residue was triturated with pentane (3×), and the combined organics were dried (Na2SO4), filtered, and concentrated under reduced pressure. The residue was chromatographed (silica gel) eluting with 10%-20% EtOAc/hexane to give the title compound (2.94 g).

Workup

  1. additionAfter addition
  2. customthe Et2O was removed by evaporation under reduced pressure
  3. customThe residue was triturated with pentane (3×)
  4. dry with materialthe combined organics were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was chromatographed (silica gel)
  8. washeluting with 10%-20% EtOAc/hexane

Sources & evidence

ORD record
ord-7797a06843c64ce7a0e81f41e2f1ff79
Source dataset
uspto-grants-2010_08
Patent number
US07772267B2

Reaction notes

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