Hydrochloric Acid → HCID 22934568, compound

HRID 1354434Notes

Reaction equation

HRID 1354434 reaction equation
[C:1]1([C:7]2[CH:11]=[C:10]([C:12]3[CH:21]=[CH:20][C:15]([C:16]([O:18]C)=[O:17])=[CH:14][CH:13]=3)[O:9][N: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[CH:11]=[C:10]([C:12]3[CH:13]=[CH:14][C:15]([C:16]([OH:18])=[O:17])=[CH:20][CH:21]=3)[O:9][N:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 22934536HCID 22934536, compound

Product 1

HCID 22934568HCID 22934568, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of methyl 4-(3-phenyl-5-isoxazolyl)benzoate (1.70 g), 1 M aqueous sodium hydroxide solution (10 ml), tetrahydrofuran (30 ml) and methanol (30 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 N,N-dimethylformamide-water to give 4-(3-phenyl-5-isoxazolyl)benzoic acid (1.56 g, yield 97%) as colorless crystals. melting point: >300° C.

Workup

  1. temperatureAfter cooling
  2. additionwas added
  3. filtrationThe crystals were collected by filtration
  4. customrecrystallized from N,N-dimethylformamide-water

Sources & evidence

ORD record
ord-3f1a4f63014548059760d22efef98502
Source dataset
uspto-grants-2007_05
Patent number
US07223791B2

Reaction notes

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