Acetic Anhydride → O-Ethylacetanilide
Reaction equation
[CH2:1]([C:3]1[CH:9]=[CH:8][CH:7]=[CH:6][C:4]=1[NH2:5])[CH3:2].[C:10](OC(=O)C)(=[O:12])[CH3:11]>O>[C:10]([NH:5][C:4]1[CH:6]=[CH:7][CH:8]=[CH:9][C:3]=1[CH2:1][CH3:2])(=[O:12])[CH3:11]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
commercial 2-ethylaniline (50 mL, 0.40 mol) was dissolved in acetic anhydride (160 mL, 1.70 mol) and stirred at room temperature for 2 h. Then the reaction mixture was poured into H2O, the whole was extracted with ethyl acetate (2×200 mL). The combined organic extracts were washed with 5% aqueous NaHCO3, brine, dried (K2CO3), filtered and concentrated to provide the title compound as a white solid (60.0 g, 92%).
Workup
- extractionthe whole was extracted with ethyl acetate (2×200 mL)
- washThe combined organic extracts were washed with 5% aqueous NaHCO3, brine
- dry with materialdried (K2CO3)
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-b144dcdb61a34243871c8d2b98bb850f
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08828986B2
Reaction notes
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