Acetic Acid → 4-(5-Phenyl-3-isoxazolyl)benzoic acid

HRID 1354437Notes

Reaction equation

HRID 1354437 reaction equation
[C:1]1([C:7]2[O:11][N:10]=[C:9]([C:12]3[CH:21]=[CH:20][C:15]([C:16]([O:18]C)=[O:17])=[CH:14][CH:13]=3)[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.C(O)(=O)C>O>[C:1]1([C:7]2[O:11][N:10]=[C:9]([C:12]3[CH:13]=[CH:14][C:15]([C:16]([OH:18])=[O:17])=[CH:20][CH:21]=3)[CH:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 22934529Methyl 4-(5-phenyl-3-isoxazolyl)benzoate

Product 1

HCID 229345254-(5-Phenyl-3-isoxazolyl)benzoic acidYield 95.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of methyl 4-(5-phenyl-3-isoxazolyl)benzoate (1.05 g), 6 M hydrochloric acid (10 ml) and acetic acid (20 ml) was heated under reflux for 5 hrs. After cooling, the reaction mixture was poured into water, and the crystals were washed with water to give 4-(5-phenyl-3-isoxazolyl)benzoic acid (0.95 g, yield 95%). Recrystallization from N,N-dimethylformamide-water gave colorless prism crystals. melting point: 297–298° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 5 hrs
  3. temperatureAfter cooling
  4. washthe crystals were washed with water

Sources & evidence

ORD record
ord-7a029e545acb4172abca6fbd286d3529
Source dataset
uspto-grants-2007_05
Patent number
US07223791B2

Reaction notes

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