Water → 934405-77-3

HRID 251929Notes

Reaction equation

HRID 251929 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:12]([C:13]([O:15]CC)=[O:14])=[CH:11][N:10]([CH3:18])[N:9]=1.[OH-].[K+].O>C(O)C>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:12]([C:13]([OH:15])=[O:14])=[CH:11][N:10]([CH3:18])[N:9]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 57780415HCID 57780415, compound

Product 1

HCID 43141394934405-77-3Yield 94.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 0.72 g of ethyl 3-(2-chlorophenyl)-1-methyl-1H-pyrazole-4-carboxylate, 0.23 g of potassium hydroxide, 1 ml of water and 5 ml of ethanol was stirred at room temperature for 3 days. After the reaction mixture was concentrated under reduced pressure, water was poured into the resulting residue and the mixture was washed with methyl tert-butyl ether. The aqueous layer was adjusted to around pH 3 by an addition of a 10% aqueous citric acid, and then extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain 0.61 g of 3-(2-chlorophenyl)-1-methyl-1H-pyrazole-4-carboxylic acid of the formula:

Workup

  1. concentrationAfter the reaction mixture was concentrated under reduced pressure, water
  2. additionwas poured into the resulting residue
  3. washthe mixture was washed with methyl tert-butyl ether
  4. additionThe aqueous layer was adjusted to around pH 3 by an addition of a 10% aqueous citric acid
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was washed with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-43e78c9c151b4a40a9f97d6cf5031119
Source dataset
uspto-grants-2011_01
Patent number
US07867949B2

Reaction notes

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