Acetic Anhydride → Ethyl 2-(4-acetylaminophenyl)propionate

HRID 2413914Notes

Reaction equation

HRID 2413914 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH3:14])[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:4][CH:3]=1.[C:15](OC(=O)C)(=[O:17])[CH3:16]>C(OCC)(=O)C>[C:15]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([CH3:14])[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:6][CH:7]=1)(=[O:17])[CH3:16]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 118009Ethyl 2-(4-aminophenyl)propanoate

Product 1

HCID 12854200Ethyl 2-(4-acetylaminophenyl)propionateYield 85%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To 10 g (0.0517 mole) of ethyl 2-(4-aminophenyl)propionate was added 50 ml of ethyl acetate with stirring, and to this solution, a mixed solution of 5.81 g of acetic anhydride and 10 ml of ethyl acetate was added dropwise and was stirred for 3 hours. After completion of the reaction, the reaction mixture was washed with a saturated solution of sodium bicarbonate and with a saturated solution of sodium chloride. After the ethyl acetate layer was dried over anhydrous magnesium sulfate, the ethyl acetate was distilled off under reduced pressure. The residue was recrystallized from ethyl acetate-n-hexane to give 10.3 g of ethyl 2-(4-acetylaminophenyl)propionate (Yield: 85%). M.P. 94.5°-95.5° C.

Workup

  1. stirringwas stirred for 3 hours
  2. customAfter completion of the reaction
  3. washthe reaction mixture was washed with a saturated solution of sodium bicarbonate and with a saturated solution of sodium chloride
  4. dry with materialAfter the ethyl acetate layer was dried over anhydrous magnesium sulfate
  5. distillationthe ethyl acetate was distilled off under reduced pressure
  6. customThe residue was recrystallized from ethyl acetate-n-hexane

Sources & evidence

ORD record
ord-a894214043ff41acb1dd46de19350b61
Source dataset
uspto-grants-1988_01
Patent number
US04720506

Reaction notes

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