Acetic Anhydride → 2-Methyl-5-nitrophenyl acetate
Reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[OH:11].[OH-].[Na+].[C:14](OC(=O)C)(=[O:16])[CH3:15]>>[C:14]([O:11][C:3]1[CH:4]=[C:5]([N+:8]([O-:10])=[O:9])[CH:6]=[CH:7][C:2]=1[CH3:1])(=[O:16])[CH3:15]Participants
Procedure
To a mixture of 2-methyl-5-nitrophenol (2.5 g, 16.3 mmol) and 1M aqueous sodium hydroxide (24.5 ml) was added at ambient temperature acetic anhydride (1.9 ml, 20.3 mmol). The mixture was stirred for 40 minutes, the solid was filtered off 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 filtered off and the filtrate evaporated to give 3-acetoxy-4-methylaniline (2.45 g, 94%).
Workup
- filtrationthe solid was filtered off
- extractionthe filtrate extracted with ethyl acetate
- washwashed with an aqueous saturated sodium chloride solution
- dry with materialdried (MgSO4)
- customevaporated
Sources & evidence
- ORD record
- ord-526621dad0294864b4d25afcc1796a9e
- Source dataset
- uspto-grants-1999_10
- Patent number
- US05962458
Reaction notes
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