Hydrochloric Acid → HCID 21105733, compound

HRID 1354438Notes

Reaction equation

HRID 1354438 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][N:11]=[C:10]([C:13]3[CH:14]=[C:15]([CH:20]=[CH:21][CH:22]=3)[C:16]([O:18]C)=[O:17])[CH:9]=2)=[CH:4][CH:3]=1.[OH-].[Na+].O1CCCC1.Cl>O.CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[O:12][N:11]=[C:10]([C:13]3[CH:14]=[C:15]([CH:20]=[CH:21][CH:22]=3)[C:16]([OH:18])=[O:17])[CH:9]=2)=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 22934521HCID 22934521, compound

Product 1

HCID 21105733HCID 21105733, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of methyl 3-[5-(4-chlorophenyl)-3-isoxazolyl]benzoate (1.10 g), 1 M aqueous sodium hydroxide solution (5 ml), tetrahydrofuran (15 ml) and methanol (15 ml) was stirred at 60° C. for 1 hr. After cooling, the reaction mixture was poured into water, and 1 M hydrochloric acid (5 ml) was added. The crystals were collected by filtration and recrystallized from tetrahydrofuran-hexane to give 3-[5-(4-chlorophenyl)-3-isoxazolyl]benzoic acid (0.91 g, yield 87%) as colorless crystals. melting point: 298–299° 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-4a04c1fd93d040f290698c6489dffec0
Source dataset
uspto-grants-2007_05
Patent number
US07223791B2

Reaction notes

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