Acetic Anhydride → HCID 13267759, compound

HRID 2413911Notes

Reaction equation

HRID 2413911 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:15])([CH3:14])[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:4][CH:3]=1.[C:16](OC(=O)C)(=[O:18])[CH3:17]>C(OCC)(=O)C>[C:16]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([CH3:14])([CH3:15])[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:6][CH:7]=1)(=[O:18])[CH3:17]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 15544083Ethyl 2-(4-aminophenyl)-2-methylpropanoate

Product 1

HCID 13267759HCID 13267759, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

5.0 g of ethyl 2-(4-aminophenyl)-2-methylpropionate was dissolved in 50 ml of ethyl acetate, and 2.5 ml of acetic anhydride was added dropwise with stirring and the solution was still stirred in the same condition for 3 hours. The reaction mixture was washed with a saturated solution of sodium bicarbonate, and successively, with a saturated solution of sodium chloride, and the ethyl acetate layer was dried over anhydrous sodium sulfate. The ethyl acetate was distilled off under reduced pressure and the residue was recrystallized from ethyl acetate-n-hexane to give 4.61 g of ethyl 2-(4-acetylaminophenyl)-2-methylpropionate (Yield: 76%). M.P. 76.0°-76.5° C.

Workup

  1. stirringthe solution was still stirred in the same condition for 3 hours
  2. washThe reaction mixture was washed with a saturated solution of sodium bicarbonate
  3. dry with materialsuccessively, with a saturated solution of sodium chloride, and the ethyl acetate layer was dried over anhydrous sodium sulfate
  4. distillationThe ethyl acetate was distilled off under reduced pressure
  5. customthe residue was recrystallized from ethyl acetate-n-hexane

Sources & evidence

ORD record
ord-20358a0cf8864d0c8bb57a9473a6452f
Source dataset
uspto-grants-1988_01
Patent number
US04720506

Reaction notes

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