Hydrochloric Acid → 5-(4-Chlorophenyl)-4-methylisoxazole-3-carboxylic acid

HRID 1510431Notes

Reaction equation

HRID 1510431 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][N:11]=[C:10]([C:13]([O:15]CC)=[O:14])[C:9]=2[CH3:18])=[CH:4][CH:3]=1.O.[OH-].[Li+].Cl>O1CCCC1.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[O:12][N:11]=[C:10]([C:13]([OH:15])=[O:14])[C:9]=2[CH3:18])=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 67121076Ethyl 5-(4-chlorophenyl)-4-methylisoxazole-3-carboxylate

Product 1

HCID 671210815-(4-Chlorophenyl)-4-methylisoxazole-3-carboxylic acidYield 95.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 5-(4-chlorophenyl)-4-methylisoxazole-3-carboxylate (63 mg, 0.24 mmol) in tetrahydrofuran (1.5 mL) was added a solution of lithium hydroxide hydrate (10 mg, 0.24 mmol) in water (1.5 mL). After stirring for 20 minutes, the reaction mixture was acidified with 1M HCl and extracted with dichloromethane three times. The combined dichloromethane extracts were washed with brine, dried over magnesium sulfate, and evaporated to obtain 5-(4-chlorophenyl)-4-methylisoxazole-3-carboxylic acid (55 mg, 0.23 mmol).

Workup

  1. extractionextracted with dichloromethane three times
  2. washThe combined dichloromethane extracts were washed with brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-e4277477388d41c0b07a4ce80836a0d8
Source dataset
uspto-grants-2012_07
Patent number
US08211927B2

Reaction notes

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