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

HRID 1978182Notes

Reaction equation

HRID 1978182 reaction equation
C[O:2][C:3](=[O:20])[C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH:14]=[CH:13][C:12]([CH3:15])=[N:11]2)=[CH:6][C:5]=1[C:16]([F:19])([F:18])[F:17].[OH-].[Na+]>CO>[CH3:15][C:12]1[CH:13]=[CH:14][N:10]([C:7]2[CH:8]=[CH:9][C:4]([C:3]([OH:20])=[O:2])=[C:5]([C:16]([F:18])([F:17])[F:19])[CH:6]=2)[N:11]=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 100.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-(3-methyl-1H-pyrazol-1-yl)-2-trifluoromethyl benzoic acid methyl ester of Step B (1.19 g, 4.2 mmol) in methanol (10 mL) was added 2.5 N sodium hydroxide (3.3 mL, 8.3 mmol). The mixture was heated at reflux for 90 minutes, cooled and concentrated. The residue was partitioned between ethyl acetate and 1N hydrochloric acid. The organic extracts were dried over sodium sulfate and evaporated to dryness to give the title compound (1.14 g) as a white solid, m.p. 192-194° C.

Workup

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

Sources & evidence

ORD record
ord-363fea4813104a98b3a5b0ff15b65122
Source dataset
uspto-grants-2001_05
Patent number
US06235900B1

Reaction notes

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