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

HRID 1635873Notes

Reaction equation

HRID 1635873 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-5c717055314b4e83b9aae88e86b338ba
Source dataset
uspto-grants-2003_01
Patent number
US06511974B1

Reaction notes

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