Sulfuric Acid → oxazolone 4-(2-carboxy-3-methoxybenzylidene)-2-phenyl-5(4H)-oxazolone

HRID 1288252Notes

Reaction equation

HRID 1288252 reaction equation
[OH-].[K+].[CH3:3][O:4][C:5]1[CH:6]=[CH:7][CH:8]=[C:9]([CH:14]=O)[C:10]=1[C:11]([OH:13])=[O:12].[C:16]1([CH:22]2[N:26]=[CH:25][C:24](=[O:27])[O:23]2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.S(=O)(=O)(O)[OH:29]>C(O)C>[C:11]([C:10]1[C:5]([O:4][CH3:3])=[CH:6][CH:7]=[CH:8][C:9]=1[CH:14]=[C:25]1[C:24](=[O:27])[O:23][C:22]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[N:26]1)([OH:13])=[O:12].[O:23]1[CH:24]=[CH:25][NH:26][C:22]1=[O:29]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 14797Potassium HydroxideHCID 40975672-Formyl-6-methoxybenzoic acidHCID 532492532-Phenyl-1,3-oxazol-5-one

Product 1

HCID 68143331oxazolone 4-(2-carboxy-3-methoxybenzylidene)-2-phenyl-5(4H)-oxazolone

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of 0.65 g. (11.5 mM) of potassium hydroxide in 23 ml. of ethanol is added 2.07 g. (11.5 mM) of 6-methoxyphthalaldehydic acid. To the resulting cooled (10°) milky suspension is added 1.89 g. (11.75 mM) of 2-phenyl-5-oxazolone. The mixture is warmed to 25° and stirred at this temperature for 35 minutes. A light orange precipitate forms. The mixture is made acidic with 3.45 ml. of 4N sulfuric acid and the resulting mixture kept at 0° for 1.5 hours and filtered. The collected solid is washed with a small amount of cold ethanol and then hexane. Air-drying gives the oxazolone 4-(2-carboxy-3-methoxybenzylidene)-2-phenyl-5(4H)-oxazolone as a yellow solid, m.p. > 320°.

Workup

  1. temperatureTo the resulting cooled (10°) milky suspension
  2. additionis added 1.89 g
  3. temperatureThe mixture is warmed to 25°
  4. filtrationfiltered
  5. washThe collected solid is washed with a small amount of cold ethanol
  6. customAir-drying

Sources & evidence

ORD record
ord-da2f39e1a217415fa6eb68e79cdb9ef6
Source dataset
uspto-grants-1976_10
Patent number
US03987185

Reaction notes

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