Hippuric Acid → 2-Phenyl-1,3-oxazol-5-one

HRID 612520Notes

Reaction equation

HRID 612520 reaction equation
[C:1]([OH:13])(=[O:12])[CH2:2][NH:3][C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=O>C(OC(=O)C)(=O)C>[C:6]1([CH:4]2[N:3]=[CH:2][C:1](=[O:12])[O:13]2)[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

3

Reactant 1

HCID 464Hippuric Acid

Product 1

HCID 532492532-Phenyl-1,3-oxazol-5-oneYield 34.7%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 80 g of hippuric acid and 400 ml of acetic anhydride is heated at 70° C. for two hours. The solution is then brought to ambient temperature and the acetic anhydride is evaporated off under vacuum. The residue is taken up into petroleum ether and crystallises. The crystals are filtered off with suction and washed with petroleum ether and with ethanol to give 25 g of 2-phenyl-5-oxazolone as crystals of melting point 90° C.

Workup

  1. customis then brought to ambient temperature
  2. customthe acetic anhydride is evaporated off under vacuum
  3. customcrystallises
  4. filtrationThe crystals are filtered off with suction
  5. washwashed with petroleum ether and with ethanol

Sources & evidence

ORD record
ord-29c72e1cd3484409b026b8194206369e
Source dataset
uspto-grants-1999_12
Patent number
US06004994

Reaction notes

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