Potassium Hydroxide → HCID 13537979, compound

HRID 1731273Notes

Reaction equation

HRID 1731273 reaction equation
C([O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=2[Cl:22])[C:10]=1[C:11]([F:14])([F:13])[F:12])=[O:5])C.[OH-].[K+]>C(O)C>[F:14][C:11]([F:12])([F:13])[C:10]1[N:9]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=2[Cl:22])[N:8]=[CH:7][C:6]=1[C:4]([OH:5])=[O:3]

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. additionpoured into 150 ml
  3. filtrationof ice/water and filtered
  4. customto remove solids
  5. filtrationfiltered
  6. customto separate the precipitate which
  7. customwas then dried
  8. customrecrystallized from cyclohexane/toluene with charcoal

Sources & evidence

ORD record
ord-14355b1897824fe08c98ee395197e24b
Source dataset
uspto-grants-1986_11
Patent number
US04620865

Reaction notes

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