Water → 4-Nitrophenyl Acetate

HRID 1970753Notes

Reaction equation

HRID 1970753 reaction equation
[C:1]([O:4][C:5](=O)[CH3:6])(=[O:3])[CH3:2].[N+:8]([C:11]1[CH:16]=CC(O)=[CH:13][CH:12]=1)([O-:10])=[O:9].O>N1C=CC=CC=1>[N+:8]([C:11]1[CH:16]=[CH:6][C:5]([O:4][C:1](=[O:3])[CH3:2])=[CH:13][CH:12]=1)([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 962WaterHCID 9804-NitrophenolHCID 7918Acetic Anhydride

Product 1

HCID 132434-Nitrophenyl AcetateYield 70%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Acetic anhydride (50 ml) is added to a solution of 4-nitrophenol (5.56 g, 40 mmol) in dry pyridine (50 ml). The solution is stirred at ambient temperature for 2 hr and then at 70° C. overnight with a reflux condenser under Ar. The mixture is poured onto ice, and a white precipitate is formed after standing for several hours. Water (400 ml) is added, and the white solid is collected by vacuum filtration and dried in vacuo to yield a white solid (5.1 g, 70%). ESI-MS (M+H)+: 182.2. 1H-NMR (CDCl3) δ 8.30 (2H, d, J=9.0 Hz, NO2CCH), 7.31 (2H, d, J=9.0 Hz, OCCH), 2.25 (3H, s, CH3).

Workup

  1. customat 70° C.
  2. customovernight
  3. additionThe mixture is poured onto ice
  4. customa white precipitate is formed
  5. waitafter standing for several hours
  6. filtrationthe white solid is collected by vacuum filtration
  7. customdried in vacuo

Sources & evidence

ORD record
ord-e41e86218d584b3ca50d043c8119d586
Source dataset
uspto-grants-2013_04
Patent number
US08431335B2

Reaction notes

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