Acetic Anhydride → 2-Methyl-5-nitrophenyl acetate

HRID 547162Notes

Reaction equation

HRID 547162 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-c4c003fd977c4c9f8261e8c2d7ec792d
Source dataset
uspto-grants-2011_05
Patent number
USRE042353E1

Reaction notes

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