Acetic Anhydride → 2-Methyl-5-nitrophenyl acetate

HRID 1596257Notes

Reaction equation

HRID 1596257 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[CH3:8][C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][C:10]=1[OH:18].[OH-].[Na+]>>[C:1]([O:18][C:10]1[CH:11]=[C:12]([N+:15]([O-:17])=[O:16])[CH:13]=[CH:14][C:9]=1[CH3:8])(=[O:3])[CH3:2]

Participants

4

Reactant 3

HCID 7918Acetic AnhydrideHCID 14798Sodium HydroxideHCID 935762-Methyl-5-nitrophenol

Product 1

HCID 179342592-Methyl-5-nitrophenyl acetateYield 252.1%

Procedure

Acetic anhydride (1.9 ml, 20.3 mmol) was added to a mixture of 2-methyl-5-nitrophenol (2.5 g, 1 6.3 mmol) and 1 M aqueous sodium hydroxide (24.5 ml) at ambient temperature. The mixture was stirred for 40 minutes, the solid was removed by filtration and the filtrate extracted with ethyl acetate. The combined organic extracts were washed with brine, dried (MgSO4) and the solvent removed by evaporation to give 2-acetoxy4-nitrotoluene (3.1 g, 100%). A mixture of this material (3.1 g, 15.9 mmol) and 10% palladium-on-charcoal catalyst (0.12 g) in ethyl acetate (50 ml) was stirred at ambient temperature under hydrogen at 1 atmosphere pressure for 2 hours. The catalyst was removed by filtration through diatomaceous earth and the solvent removed from filtrate by evaporation to give 3-acetoxy-4-methylaniline (2.45 g, 94%).

Workup

  1. customthe solid was removed by filtration
  2. extractionthe filtrate extracted with ethyl acetate
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried (MgSO4)
  5. customthe solvent removed by evaporation

Sources & evidence

ORD record
ord-f8ecb9a7e36f48efa13f92164535424a
Source dataset
uspto-grants-2001_09
Patent number
US06291455B1

Reaction notes

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