Acetic Anhydride → O-Ethylacetanilide

HRID 72818

Reaction equation

HRID 72818 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

HCID 7918Acetic AnhydrideHCID 113572-Ethylaniline

Product 1

HCID 36332O-EthylacetanilideYield 92%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

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

  1. extractionthe whole was extracted with ethyl acetate (2×200 mL)
  2. washThe combined organic extracts were washed with 5% aqueous NaHCO3, brine
  3. dry with materialdried (K2CO3)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-b144dcdb61a34243871c8d2b98bb850f
Source dataset
uspto-grants-2014_09
Patent number
US08828986B2

Linked notes

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