Sodium Hydroxide → HCID 71770375, compound

HRID 626283Notes

Reaction equation

HRID 626283 reaction equation
C([O:3][C:4]([C:6]1[C:7]([CH:24]([F:26])[F:25])=[N:8][N:9]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[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>[C:18]1([N:9]2[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:24]([F:25])[F:26])=[N:8]2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 71770224HCID 71770224, compound

Product 1

HCID 71770375HCID 71770375, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

N-Phenyl-3-difluoromethyl-5-pentafluoroethyl-4-pyrazolecarboxylic acid ethyl ester (3.0 g, 7.81 mmol) in ethanol (15 ml) was admixed gradually with an 8N aqueous sodium hydroxide solution (3.0 ml) and stirred at room temperature for 3 h. The solvent was removed by rotary evaporation; the residue was taken up in water (40 ml) and extracted with diethyl ether (20 ml). Acidification to pH 1 with 6M HCl was followed by extraction with ethyl acetate (3×30 ml). The combined organic phases were dried over sodium sulphate and filtered, and the solvent was removed by rotary evaporation. N-Phenyl-3-difluoromethyl-5-pentafluoroethyl-4-pyrazolecarboxylic acid (2.71 g, 7.61 mmol, 98%) was isolated as a colourless solid.

Workup

  1. customThe solvent was removed by rotary evaporation
  2. extractionextracted with diethyl ether (20 ml)
  3. extractionAcidification to pH 1 with 6M HCl was followed by extraction with ethyl acetate (3×30 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-67061aa63ec046f5a5bc34d78023e9b1
Source dataset
uspto-grants-2016_04
Patent number
US09309202B2

Reaction notes

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