Hydrochloric Acid → 3-(5-Phenyl-3-isoxazolyl)benzoic acid

HRID 1354436Notes

Reaction equation

HRID 1354436 reaction equation
[C:1]1([C:7]2[O:11][N:10]=[C:9]([C:12]3[CH:13]=[C:14]([CH:19]=[CH:20][CH:21]=3)[C:15]([O:17]C)=[O:16])[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+].O1CCCC1.Cl>O.CO>[C:1]1([C:7]2[O:11][N:10]=[C:9]([C:12]3[CH:13]=[C:14]([CH:19]=[CH:20][CH:21]=3)[C:15]([OH:17])=[O:16])[CH:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 22934547Methyl 3-(5-phenyl-3-isoxazolyl)benzoate

Product 1

HCID 229345643-(5-Phenyl-3-isoxazolyl)benzoic acidYield 85%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of methyl 3-(5-phenyl-3-isoxazolyl)benzoate (1.30 g), 1 M aqueous sodium hydroxide solution (10 ml), tetrahydrofuran (20 ml) and methanol (10 ml) was stirred at 60° C. for 1 hr. After cooling, the reaction mixture was poured into water, and 1 M hydrochloric acid (10 ml) was added. The crystals were collected by filtration and recrystallized from tetrahydrofuran-hexane to give 3-(5-phenyl-3-isoxazolyl)benzoic acid (1.05 g, yield 85%) as colorless crystals. melting point: 250–251° C.

Workup

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

Sources & evidence

ORD record
ord-551a8fde9d2a46e481410d481f2261ac
Source dataset
uspto-grants-2007_05
Patent number
US07223791B2

Reaction notes

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