Catechol → Nitrocatechol

HRID 751043Notes

Reaction equation

HRID 751043 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-a4d7f0088e334c66a99cc5a8caf73a85
Source dataset
uspto-grants-2008_07
Patent number
US07405234B2

Reaction notes

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