Acetone → 2-Acetamido-3-[4-(acetyloxy)phenyl]prop-2-enoic acid

HRID 259595Notes

Reaction equation

HRID 259595 reaction equation
[CH3:1][C:2]1[O:3][C:4](=[O:18])[C:5](=[CH:7][C:8]2[CH:13]=[CH:12][C:11]([O:14][C:15](=[O:17])[CH3:16])=[CH:10][CH:9]=2)[N:6]=1.CC(C)=[O:21]>O>[C:15]([O:14][C:11]1[CH:12]=[CH:13][C:8]([CH:7]=[C:5]([NH:6][C:2](=[O:21])[CH3:1])[C:4]([OH:3])=[O:18])=[CH:9][CH:10]=1)(=[O:17])[CH3:16]

Participants

4

Reactant 2

HCID 180AcetoneHCID 5395274-[(2-Methyl-5-oxo-1,3-oxazol-4(5H)-ylidene)methyl]phenyl acetate

Product 1

HCID 541178672-Acetamido-3-[4-(acetyloxy)phenyl]prop-2-enoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

75.8 g (0.3 mol) of 2-methyl-4-(p-acetoxy-benzylidene)-5(4H)-oxazolone are dissolved in a mixture of 725 ml of acetone and 281 ml of water and thereafter the solution is heated to the boil, under a reflux condenser, for 15 hours. Hereupon, a yellowish precipitate separates out. The reaction mixture is cooled and then filtered. The resulting crystals are recrystallised from acetone-water. p-Acetoxy-α-acetylaminocinnamic acid of melting point 236°-237° C. is obtained.

Workup

  1. temperaturethe solution is heated to the boil, under a reflux condenser, for 15 hours
  2. temperatureThe reaction mixture is cooled
  3. filtrationfiltered
  4. customThe resulting crystals are recrystallised from acetone-water

Sources & evidence

ORD record
ord-d62abc07d2164db4a83e50bef7d9a272
Source dataset
uspto-grants-1977_07
Patent number
US04038414

Reaction notes

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