Hydrochloric Acid → 4-Chloro-5-(4-chlorophenyl)isoxazole-3-carboxylic acid

HRID 1510421Notes

Reaction equation

HRID 1510421 reaction equation
[Cl:1][C:2]1[C:3]([C:14]([O:16]CC)=[O:15])=[N:4][O:5][C:6]=1[C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=1.[OH-].[Na+].Cl>CO>[Cl:1][C:2]1[C:3]([C:14]([OH:16])=[O:15])=[N:4][O:5][C:6]=1[C:7]1[CH:8]=[CH:9][C:10]([Cl:13])=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67121071HCID 67121071, compound

Product 1

HCID 671211334-Chloro-5-(4-chlorophenyl)isoxazole-3-carboxylic acidYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of ethyl 4-chloro-5-(4-chlorophenyl)isoxazole-3-carboxylate (20 mg, 0.07 mmol) in methanol (0.5 mL), an aqueous solution of 1N NaOH (140 μL, 0.14 mmol) was added. The mixture was left to stand at room temperature for 2 hours, the reaction mixture was acidified using a 1N HCl solution and methanol was removed in vacuo. The aqueous mixture was extracted with ethylacetate (3×3 mL), the organics combined, dried with MgSO4 and filtered before evaporation to dryness in vacuo to obtain 4-chloro-5-(4-chlorophenyl)isoxazole-3-carboxylic acid (18 mg, 0.07 mmol).

Workup

  1. waitThe mixture was left
  2. customwas removed in vacuo
  3. extractionThe aqueous mixture was extracted with ethylacetate (3×3 mL)
  4. dry with materialdried with MgSO4
  5. filtrationfiltered before evaporation to dryness in vacuo

Sources & evidence

ORD record
ord-0577edd074804cbbab1c30e965122b5d
Source dataset
uspto-grants-2012_07
Patent number
US08211927B2

Reaction notes

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