Hydrochloric Acid → 4-[5-(4-Trifluoromethylphenyl)-3-isoxazolyl]benzoic acid

HRID 1354444Notes

Reaction equation

HRID 1354444 reaction equation
[F:1][C:2]([F:25])([F:24])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:13][N:12]=[C:11]([C:14]3[CH:23]=[CH:22][C:17]([C:18]([O:20]C)=[O:19])=[CH:16][CH:15]=3)[CH:10]=2)=[CH:5][CH:4]=1.[OH-].[Na+].O1CCCC1.Cl>O.CO>[F:25][C:2]([F:1])([F:24])[C:3]1[CH:4]=[CH:5][C:6]([C:9]2[O:13][N:12]=[C:11]([C:14]3[CH:23]=[CH:22][C:17]([C:18]([OH:20])=[O:19])=[CH:16][CH:15]=3)[CH:10]=2)=[CH:7][CH:8]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 15453642Methyl 4-[5-(4-trifluoromethylphenyl)-3-isoxazolyl]benzoate

Product 1

HCID 99056704-[5-(4-Trifluoromethylphenyl)-3-isoxazolyl]benzoic acidYield 77%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of methyl 4-[5-(4-trifluoromethylphenyl)-3-isoxazolyl]benzoate (0.486 g), 1 M aqueous sodium hydroxide solution (4 ml), tetrahydrofuran (20 ml) and methanol (20 ml) was stirred at 60° C. for 1 hr. After cooling, the reaction mixture was poured into water and 1 M hydrochloric acid (15 ml) was added. The crystals were collected by filtration and recrystallized from ethanol to give 4-[5-(4-trifluoromethylphenyl)-3-isoxazolyl]benzoic acid (0.358 g, yield 77%) as a colorless crystalline powder. melting point: >300° C.

Workup

  1. temperatureAfter cooling
  2. additionwas added
  3. filtrationThe crystals were collected by filtration
  4. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-cb4dfb35fbf348a988a2f86f38d884b3
Source dataset
uspto-grants-2007_05
Patent number
US07223791B2

Reaction notes

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