Sodium Hydroxide → 2,4-Dichloro-3-(3-methylisoxazol-5-yl)benzoic acid

HRID 1276138Notes

Reaction equation

HRID 1276138 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[C:13]([C:14]2[O:18][N:17]=[C:16]([CH3:19])[CH:15]=2)=[C:12]([Cl:20])[CH:11]=[CH:10][C:5]=1[C:6]([O:8]C)=[O:7]>O.CO.O1CCCC1>[Cl:3][C:4]1[C:13]([C:14]2[O:18][N:17]=[C:16]([CH3:19])[CH:15]=2)=[C:12]([Cl:20])[CH:11]=[CH:10][C:5]=1[C:6]([OH:8])=[O:7]

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 15430825Methyl 2,4-dichloro-3-(3-methylisoxazol-5-yl)benzoate

Product 1

HCID 154308262,4-Dichloro-3-(3-methylisoxazol-5-yl)benzoic acidYield 96.5%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

0.35 g (8.8 mmol) of sodium hydroxide in 35 ml of water was added to 2.3 g (8.0 mmol) of methyl 2,4-dichloro-3-(3-methylisoxazol-5-yl)benzoate in a mixture of 50 ml of methanol and 50 ml of tetrahydrofuran. The mixture was stirred at room temperature for 12 hours, the solvent was removed and the residue was taken up in ethyl acetate/water. After phase separation, the organic phase was separated off and the aqueous phase was washed with ethyl acetate. The remaining aqueous phase was acidified and then extracted with ethyl acetate; the resulting organic phase was dried and concentrated. 2.1 g (96% of theory) of 2,4-dichloro-3-(3-methylisoxazol-5-yl)benzoic acid were obtained.

Workup

  1. customthe solvent was removed
  2. customAfter phase separation
  3. customthe organic phase was separated off
  4. washthe aqueous phase was washed with ethyl acetate
  5. extractionextracted with ethyl acetate
  6. customthe resulting organic phase was dried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-84e1a5d0ea024f33a9d47a544dfed830
Source dataset
uspto-grants-2000_12
Patent number
US06165944

Reaction notes

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