Sodium Hydroxide → HCID 71770374, compound

HRID 626279Notes

Reaction equation

HRID 626279 reaction equation
C([O:3][C:4]([C:6]1[C:7]([CH:19]([F:21])[F:20])=[N:8][N:9]([CH3:18])[C:10]=1[C:11]([F:17])([F:16])[C:12]([F:15])([F:14])[F:13])=[O:5])C.[OH-].[Na+]>C(O)C>[CH3:18][N:9]1[C:10]([C:11]([F:16])([F:17])[C:12]([F:13])([F:14])[F:15])=[C:6]([C:4]([OH:5])=[O:3])[C:7]([CH:19]([F:21])[F:20])=[N:8]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 71770125HCID 71770125, compound

Product 1

HCID 71770374HCID 71770374, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

N-Methyl-3-difluoromethyl-5-pentafluoroethyl-4-pyrazolecarboxylic acid ethyl ester (0.5 g, 1.55 mmol) in ethanol (3 ml) was admixed gradually with an 8N aqueous sodium hydroxide solution (0.6 ml) and stirred at room temperature for 3 h. The solvent was removed by rotary evaporation; the residue was taken up in water (10 ml) and extracted with diethyl ether (10 ml). Acidification to pH 1 with 6M HCl was followed by extraction with ethyl acetate (3×10 ml). The combined organic phases were dried over sodium sulphate and filtered, and the solvent was removed by rotary evaporation. N-Methyl-3-difluoromethyl-5-pentafluoroethyl-4-pyrazolecarboxylic acid (0.44 g, 1.50 mmol, 97%) was isolated as a colourless solid.

Workup

  1. customThe solvent was removed by rotary evaporation
  2. extractionextracted with diethyl ether (10 ml)
  3. extractionAcidification to pH 1 with 6M HCl was followed by extraction with ethyl acetate (3×10 ml)
  4. dry with materialThe combined organic phases were dried over sodium sulphate
  5. filtrationfiltered
  6. customthe solvent was removed by rotary evaporation

Sources & evidence

ORD record
ord-441e98ea0d2b443f868b046261e864b6
Source dataset
uspto-grants-2016_04
Patent number
US09309202B2

Reaction notes

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