Potassium Hydroxide → HCID 13537979, compound

HRID 1284402Notes

Reaction equation

HRID 1284402 reaction equation
[F:1][C:2]([F:22])([F:21])[C:3]1[N:7]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][C:9]=2[Cl:15])[N:6]=[CH:5][C:4]=1[C:16]([O:18]CC)=[O:17].[OH-].[K+]>C(O)C>[F:22][C:2]([F:1])([F:21])[C:3]1[N:7]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][C:9]=2[Cl:15])[N:6]=[CH:5][C:4]=1[C:16]([OH:18])=[O:17]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 13537978Ethyl 1-(2,4-dichlorophenyl)-5-(trifluoromethyl)-1H-pyrazole-4-carboxylate

Product 1

HCID 13537979HCID 13537979, compoundYield 62.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5-(Trifluoromethyl)-1-(2,4-dichlorophenyl)-1H-pyrazole-4-carboxylic acid, ethyl ester (3.31 grams, 0.0094 mole) and potassium hydroxide (0.8 gram, 0.014 mole) were combined in 25 ml of ethanol. The reaction mixture was refluxed for 2 hours, then poured into 150 ml of ice/water and filtered to remove solids. The remaining solution was acidified with concentrated HCl, filtered to separate the precipitate which was then dried and recrystallized from cyclohexane/toluene with charcoal, yielding 1.90 grams of 5-(trifluoromethyl)-1-(2,4-dichlorophenyl)-1H-pyrazole-4-carboxylic acid, mp=154°-155° C.

Workup

  1. temperatureThe reaction mixture was refluxed for 2 hours
  2. filtrationfiltered
  3. customto remove solids
  4. filtrationfiltered
  5. customto separate the precipitate which
  6. customwas then dried
  7. customrecrystallized from cyclohexane/toluene with charcoal

Sources & evidence

ORD record
ord-859eccd40b02469d880dc738317af2b7
Source dataset
uspto-grants-1986_01
Patent number
US04563210

Reaction notes

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