Acetic Anhydride → 2-Methyl-5-nitrophenyl acetate

HRID 2227910Notes

Reaction equation

HRID 2227910 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 100%

Procedure

Acetic anhydride (1.9 ml, 20.3 mmol) was added to a mixture of 2-methyl-5-nitrophenol (2.5 g, 16.3 mmol) and 1M 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 organic layers were combined, washed with an aqueous saturated sodium chloride solution, dried (MgSO4) and evaporated to yield 2-acetoxy-4-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 an atmosphere of hydrogen for 2 hours. The catalyst was removed by filtration and the filtrate evaporated 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. washwashed with an aqueous saturated sodium chloride solution
  4. dry with materialdried (MgSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-f668dac8a9e242cf98ca9ced3ea634e4
Source dataset
uspto-grants-2002_07
Patent number
US06414148B1

Reaction notes

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