Acetone → 1-[3-(Trifluoromethyl)phenyl]-1H-pyrazole-4-carboxylic acid

HRID 27280Notes

Reaction equation

HRID 27280 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]1[CH:4]=[C:5]([N:9]2[CH:13]=[C:12]([CH:14]=[O:15])[CH:11]=[N:10]2)[CH:6]=[CH:7][CH:8]=1.CC(C)=[O:20].CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O.S(=O)(=O)(O)O>[O-2].[O-2].[O-2].[Cr+6].O>[F:17][C:2]([F:1])([F:16])[C:3]1[CH:4]=[C:5]([N:9]2[CH:13]=[C:12]([C:14]([OH:20])=[O:15])[CH:11]=[N:10]2)[CH:6]=[CH:7][CH:8]=1

Participants

7

Reactant 4

HCID 180AcetoneHCID 1118Sulfuric AcidHCID 233444471-[3-(Trifluoromethyl)phenyl]-1H-pyrazole-4-carbaldehydeHCID 131709961Jones' reagent3×

Product 1

HCID 149944991-[3-(Trifluoromethyl)phenyl]-1H-pyrazole-4-carboxylic acidYield 89%

Reagents, catalysts & solvents 2

HCID 10219390chromium (VI) trioxideCatalystHCID 962WaterSolvent

Procedure

Into a 500 ml. Erlenmeyer flask, fitted with a thermometer and a magnetic stirrer, containing a solution of 8.3 g. (0.0346 M.) of 1-(m-trifluoromethylphenyl)pyrazole-4-carboxaldehyde in 300 ml. of acetone is slowly added 20.0 ml. of Jones reagent (prepared by dissolving 26.7 g. of chromium trioxide in 23.0 ml. of concentrated sulfuric acid and then diluting to 100 ml. with water), the addition of the Jones reagent being effected while the solution is cooled by an ice water bath. Upon completion of the addition of the Jones reagent, the reaction mixture is stirred, under cooling, for 15 minutes and then for an additional 20 minutes at room temperature, after which time it is quenched with a large volume of water and allowed to stand at room temperature for about 3 hours. The resultant precipitated solids are then filtered and washed successively with water and petroleum ether. The solvent is then removed under vacuum to yield 1-(m-trifluoromethylphenyl)pyrazole-4-carboxylic acid, m.p. 145°-148° C. (Yield: 89%).

Workup

  1. customErlenmeyer flask, fitted with a thermometer and a magnetic stirrer
  2. additioncontaining a solution of 8.3 g
  3. dissolutionby dissolving 26.7 g
  4. temperatureis cooled by an ice water bath
  5. temperatureunder cooling, for 15 minutes
  6. customafter which time it is quenched with a large volume of water
  7. waitto stand at room temperature for about 3 hours
  8. customThe resultant precipitated solids
  9. filtrationare then filtered
  10. washwashed successively with water and petroleum ether
  11. customThe solvent is then removed under vacuum

Sources & evidence

ORD record
ord-46d183fa0fcb4319a574fea044f921fe
Source dataset
uspto-grants-1980_09
Patent number
US04220792

Reaction notes

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