1-Methyl-1H-pyrazole-4-carbaldehyde → 1-Methyl-1H-pyrazole-4-carboxylic acid

HRID 414609Notes

Reaction equation

HRID 414609 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([CH:7]=[O:8])[CH:4]=[N:3]1.CC(C)=[O:11].OS(O)(=O)=O.O=[Cr](=O)=O>CC(C)=O>[CH3:1][N:2]1[CH:6]=[C:5]([C:7]([OH:11])=[O:8])[CH:4]=[N:3]1

Participants

4

Reactant 2

HCID 5731171-Methyl-1H-pyrazole-4-carbaldehydeHCID 131709961Jones' reagent2×

Product 1

HCID 6431601-Methyl-1H-pyrazole-4-carboxylic acidYield 52%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

3.9 g of 1-methylpyrazole-4-aldehyde (described in J. Chem. Soc., page 3314, 1957) was dissolved in 20 ml of acetone, and while heating the solution, the Jones reagent was added. After the reaction, the excess of the Jones reagent was treated with a dilute aqueous alkaline solution, and the precipitate was collected by filtration. The filtrate was made weakly acidic and extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give 2.3 g (yield 52%) of 1-methylpyrazole-4-carboxylic acid. m.p. 205°-206° C.

Workup

  1. temperaturewhile heating the solution
  2. customAfter the reaction
  3. filtrationthe precipitate was collected by filtration
  4. extractionextracted with ethyl acetate
  5. dry with materialThe extract was dried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3a2c167913da47b9b99b181986edf847
Source dataset
uspto-grants-1988_12
Patent number
US04792565

Reaction notes

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