Water → (3-Acetamidophenyl) acetate

HRID 1773553Notes

Reaction equation

HRID 1773553 reaction equation
[C:1]([O:4][C:5](=O)[CH3:6])(=[O:3])[CH3:2].[NH2:8][C:9]1[CH:10]=[C:11](O)C=C[CH:14]=1.[OH2:16].N1[CH:22]=[CH:21]C=CC=1>CN(C)C1C=CN=CC=1>[C:21]([NH:8][C:9]1[CH:14]=[C:5]([O:4][C:1](=[O:3])[CH3:2])[CH:6]=[CH:11][CH:10]=1)(=[O:16])[CH3:22]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 7918Acetic AnhydrideHCID 115683-Aminophenol

Product 1

HCID 231988(3-Acetamidophenyl) acetate

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

Acetic anhydride (53 mL, 572.0 mmol) was slowly added to a mixture of 3-aminophenol (25 g, 225.0 mmol) and 4-dimethylaminopyridine (catalytic quantity) in pyridine (100 mL) at 0° C. and the reaction mixture was stirred at room temperature for 62 hours. Water (1 L) was added and the resulting mixture was extracted with ethyl acetate. The organic extracts were washed with an aqueous solution of hydrochloric acid, a saturated aqueous solution of sodium bicarbonate and water, dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure to give 21.79 g of acetic acid 3-acetylamino-phenyl ester as a solid without further purifications. A second batch (2.978 g) of this material crashed out of the aqueous layer upon standing and was collected by filtration.

Workup

  1. extractionthe resulting mixture was extracted with ethyl acetate
  2. washThe organic extracts were washed with an aqueous solution of hydrochloric acid
  3. dry with materiala saturated aqueous solution of sodium bicarbonate and water, dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-e769f0f6c7d445658f464a969613e7fc
Source dataset
uspto-grants-2016_02
Patent number
US09255110B2

Reaction notes

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