Sodium Hydroxide → 4-(3-Methyl-1H-pyrazol-1-yl)-2-trifluoromethylbenzoic acid

HRID 2307382Notes

Reaction equation

HRID 2307382 reaction equation
[CH3:1][C:2]1[CH:6]=[CH:5][N:4]([C:7]2[CH:16]=[CH:15][C:10]([C:11]([O:13]C)=[O:12])=[C:9]([C:17]([F:20])([F:19])[F:18])[CH:8]=2)[N:3]=1.[OH-].[Na+]>CO>[CH3:1][C:2]1[CH:6]=[CH:5][N:4]([C:7]2[CH:16]=[CH:15][C:10]([C:11]([OH:13])=[O:12])=[C:9]([C:17]([F:19])([F:18])[F:20])[CH:8]=2)[N:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 15541085Methyl 4-(3-methyl-pyrazol-1-yl)-2-trifluoromethyl-benzoate

Product 1

HCID 155410864-(3-Methyl-1H-pyrazol-1-yl)-2-trifluoromethylbenzoic acidYield 100.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 4-(3-methyl-pyrazol-1-yl)-2-trifluoromethyl-benzoate (1.19 g) from Example 93, step b) was dissolved in methanol (10 ml) and a solution of 2.5 N sodium hydroxide (3.3 ml) was added. The reaction was heated at reflux for 90 minutes, cooled to room temperature and concentrated in vacuo to dryness. The residue was partitioned between ethyl acetate and 1 N hydrochloric acid. The combined organic extracts were dried over anhydrous sodium sulfate and concentrated in vacuo to give 1.14 g of the title compound as a colorless solid. MS (FAB) m/z: 271 (M+H)+.

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 90 minutes
  3. concentrationconcentrated in vacuo to dryness
  4. customThe residue was partitioned between ethyl acetate and 1 N hydrochloric acid
  5. dry with materialThe combined organic extracts were dried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-28b625a8eb2a4fafafe097d3be73aed0
Source dataset
uspto-grants-2004_12
Patent number
US06831079B1

Reaction notes

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