Water → 5-Methyl-2-phenyl-4-oxazoleacetic acid

HRID 1440234Notes

Reaction equation

HRID 1440234 reaction equation
[C:1]1([C:7]2[O:8][C:9]([CH3:15])=[C:10]([CH2:12][CH2:13][OH:14])[N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(=O)(=O)(O)[OH:17].O>CC(C)=O.[O-2].[O-2].[O-2].[Cr+6]>[C:1]1([C:7]2[O:8][C:9]([CH3:15])=[C:10]([CH2:12][C:13]([OH:17])=[O:14])[N:11]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 962Water2×HCID 1118Sulfuric AcidHCID 7255852-(5-Methyl-2-phenyl-4-oxazolyl)ethanol

Product 1

HCID 27751395-Methyl-2-phenyl-4-oxazoleacetic acid

Reagents, catalysts & solvents 2

HCID 10219390chromium (VI) trioxideCatalystHCID 180AcetoneSolvent

Procedure

To a solution of 1.0 g of 2-phenyl-4-hydroxyethyl5-methyloxazole in 20 ml of acetone was added a solution consisting of 1 g of chromium trioxide, 0.9 ml of concentrated sulfuric acid and 4 ml of water and the reaction stirred at room temperature for 40 minutes. The reaction mixture was poured into water (60 ml) and the product extracted with 150 ml of ethyl acetate. The organic layer was washed with water (2×50 ml) and dried over sodium sulfate. Removal of the solvent gave the crude product as an oil. The residue was dissolved in 80 ml of ethyl acetate and the product extracted with 100 ml of 0.25N aqueous sodium hydroxide. The aqueous layer was separated, acidified with 1N hydrochloric acid and the product extracted with 150 ml of ethyl acetate. The organic phase was separated, dried over sodium sulfate and concentrated to give a yellow solid, 500 mg.

Workup

  1. extractionthe product extracted with 150 ml of ethyl acetate
  2. washThe organic layer was washed with water (2×50 ml)
  3. dry with materialdried over sodium sulfate
  4. customRemoval of the solvent

Sources & evidence

ORD record
ord-e64e38b65d5a4d49b21413734f7b7edf
Source dataset
uspto-grants-1996_03
Patent number
US05498621

Reaction notes

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