Acetic Anhydride → 4-(Acetyloxy)-3-nitrobenzoic acid

HRID 1942450Notes

Reaction equation

HRID 1942450 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].[C:14](OC(=O)C)(=[O:16])[CH3:15]>N1C=CC=CC=1>[C:14]([O:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12])(=[O:16])[CH3:15]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 120334-Hydroxy-3-nitrobenzoic acid

Product 1

HCID 140573074-(Acetyloxy)-3-nitrobenzoic acid

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To 4-hydroxy-3-nitrobenzoic acid (10 g) were added pyridine (12 ml) and acetic anhydride (55 ml), and the mixture was stirred at room temperature for 65 hours. The reaction solution was concentrated under reduced pressure, and thereto was added a 5% aqueous sodium hydrogen sulfate solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered and concentrated under reduced pressure to give the title compound (11.7 g).

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. additionwas added a 5% aqueous sodium hydrogen sulfate solution
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-08f9aeba1a974cd8b246e3d336654e04
Source dataset
uspto-grants-2013_03
Patent number
US08389511B2

Reaction notes

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