Hydrochloric Acid → 3-o-Tolyl-isoxazole-4-carboxylic acid

HRID 474364Notes

Reaction equation

HRID 474364 reaction equation
C([O:3][C:4]([C:6]1[C:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[CH3:17])=[N:8][O:9][CH:10]=1)=[O:5])C.Cl>C(O)(=O)C>[C:12]1([CH3:17])[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[C:7]1[C:6]([C:4]([OH:5])=[O:3])=[CH:10][O:9][N:8]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 666775933-o-Tolyl-isoxazole-4-carboxylic acid ethyl ester

Product 1

HCID 666771273-o-Tolyl-isoxazole-4-carboxylic acidYield 80.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 3-o-tolyl-isoxazole-4-carboxylic acid ethyl ester (1.32 g, 5.71 mmol, 1.0 equiv), 6M HCl aqueous solution (40 mL) and acetic acid (24 mL) was heated to reflux for 5 hours. After cooling, the mixture was partitioned between water and ethyl acetate and separated. The organic phase was sequentially washed with water and saturated aqueous sodium chloride solution. The collected organic was then dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum to give 930 mg (80%) of crude 3-o-tolyl-isoxazole-4-carboxylic acid which was used without purification.

Workup

  1. temperatureto reflux for 5 hours
  2. temperatureAfter cooling
  3. customthe mixture was partitioned between water and ethyl acetate
  4. customseparated
  5. washThe organic phase was sequentially washed with water and saturated aqueous sodium chloride solution
  6. dry with materialThe collected organic was then dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-1a156ec155cc43e5b1d1958060d873a5
Source dataset
uspto-grants-2014_01
Patent number
US08637526B2

Reaction notes

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