Potassium Hydroxide → 1-(4-benzyloxybenzyl)-3-phenyl-1H-pyrazol-4-carboxylic acid

HRID 350111Notes

Reaction equation

HRID 350111 reaction equation
[CH2:1]([O:8][C:9]1[CH:31]=[CH:30][C:12]([CH2:13][N:14]2[CH:18]=[C:17]([C:19]([O:21]CC)=[O:20])[C:16]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[N:15]2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+]>C(O)C>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:13][N:14]2[CH:18]=[C:17]([C:19]([OH:21])=[O:20])[C:16]([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)=[N:15]2)=[CH:30][CH:31]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 23024748ethyl 1-(4-benzyloxybenzyl)-3-phenyl-1H-pyrazole-4-carboxylate

Product 1

HCID 230251141-(4-benzyloxybenzyl)-3-phenyl-1H-pyrazol-4-carboxylic acidYield 82%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of ethyl 1-(4-benzyloxybenzyl)-3-phenyl-1H-pyrazole-4-carboxylate (1.79 g), potassium hydroxide (0.75 g) and ethanol (30 ml) was refluxed for 5 hours. After removal of the solvent under reduced pressure, water was added to the reaction mixture, then the mixture was acidified with 1N hydrochloric acid. The crystals obtained were collected by filtration to yield 1-(4-benzyloxybenzyl)-3-phenyl-1H-pyrazol-4-carboxylic acid (1.36 g, yield: 82%). This was recrystallized from acetone-hexane. Melting point: 152–153° C.

Workup

  1. temperaturewas refluxed for 5 hours
  2. customAfter removal of the solvent under reduced pressure, water
  3. additionwas added to the reaction mixture
  4. customThe crystals obtained
  5. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-12d65d1500ea45bd9dc33fd4faa9014e
Source dataset
uspto-grants-2007_02
Patent number
US07179823B1

Reaction notes

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