Benzaldehyde → 2-Phenyl-4-(phenylmethylene)-5(4H)-oxazolone

HRID 326760Notes

Reaction equation

HRID 326760 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(=O)(O)[O-].[K+].[CH:19](=O)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.O>C(OC(=O)C)(=O)C>[CH:19](=[C:2]1[C:1](=[O:12])[O:13][C:4]([C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=2)=[N:3]1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 240BenzaldehydeHCID 464Hippuric AcidHCID 962WaterHCID 516893Potassium Bicarbonate

Product 1

HCID 1366632-Phenyl-4-(phenylmethylene)-5(4H)-oxazoloneYield 49.5%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Conditions

Temperature
50 °C

Procedure

1.8 g of hippuric acid and 0.4 g of potassium bicarbonate are dissolved in 4 ml of acetic anhydride, the solution is heated for a few minutes at 50° C. and then cooled to room temperature and 1.49 g of benzaldehyde are added. After 1 hour at room temperature, 20 ml of distilled water are added at 80° C. The solid which precipitates is filtered off, washed with water and ethanol and then dried to give 1.24 g of the expected product in the form of a yellow solid.

Workup

  1. temperaturecooled to room temperature
  2. customThe solid which precipitates
  3. filtrationis filtered off
  4. washwashed with water and ethanol
  5. customdried

Sources & evidence

ORD record
ord-942fa7b5ef6447e887ff6d9d2560f21b
Source dataset
uspto-grants-1993_12
Patent number
US05270317

Reaction notes

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