Potassium Hydroxide → 1-(3-Phenylpropyl)pyrazole-4-carboxylic acid

HRID 2188997Notes

Reaction equation

HRID 2188997 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][N:10]2[CH:14]=[C:13]([C:15]([O:17]CC)=[O:16])[CH:12]=[N:11]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[K+]>CO>[C:1]1([CH2:7][CH2:8][CH2:9][N:10]2[CH:14]=[C:13]([C:15]([OH:17])=[O:16])[CH:12]=[N:11]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 21958678Ethyl 1-(3-phenylpropyl)pyrazole-4-carboxylate

Product 1

HCID 219586571-(3-Phenylpropyl)pyrazole-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The ester was then dissolved in methanol (30 ml), and potassium hydroxide (1.5 g) added. The mixture was refluxed for 5 hours under nitrogen, then the solvent removed under reduced pressure. The residue was partitioned between methylene chloride and water. The aqueous layer was separated and acidified to pH 1-2 with 6N hydrochloric acid, then extracted with ethyl acetate. The combined organic layers were dried over magnesium sulfate, and the solvent removed under reduced pressure, to give 1-(3-phenylpropyl)pyrazole-4-carboxylic acid.

Workup

  1. temperatureThe mixture was refluxed for 5 hours under nitrogen
  2. customthe solvent removed under reduced pressure
  3. customThe residue was partitioned between methylene chloride and water
  4. customThe aqueous layer was separated
  5. extractionextracted with ethyl acetate
  6. dry with materialThe combined organic layers were dried over magnesium sulfate
  7. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-b00093bed32a41a1b87d4dd65e7c7e78
Source dataset
uspto-grants-2012_12
Patent number
US08324224B2

Reaction notes

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