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Hydrochloric Acid → 1-(4-phenoxybenzyl)-3-(4-phenoxybenzyloxy)-1H-pyrazole-4-carboxylic acid

HRID 350306
Notes
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Reaction equation

HRID 350306 reaction equation
[O:1]([C:8]1[CH:39]=[CH:38][C:11]([CH2:12][N:13]2[CH:17]=[C:16]([C:18]([O:20]CC)=[O:19])[C:15]([O:23][CH2:24][C:25]3[CH:30]=[CH:29][C:28]([O:31][C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)=[CH:27][CH:26]=3)=[N:14]2)=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].O1CCCC1.Cl>C(O)C>[O:1]([C:8]1[CH:39]=[CH:38][C:11]([CH2:12][N:13]2[CH:17]=[C:16]([C:18]([OH:20])=[O:19])[C:15]([O:23][CH2:24][C:25]3[CH:30]=[CH:29][C:28]([O:31][C:32]4[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=4)=[CH:27][CH:26]=3)=[N:14]2)=[CH:10][CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 23024849ethyl 1-(4-phenoxybenzyl)-3-(4-phenoxybenzyloxy)-1H-pyrazole-4-carboxylate

Product 1

HCID 230251191-(4-phenoxybenzyl)-3-(4-phenoxybenzyloxy)-1H-pyrazole-4-carboxylic acidYield 95.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

After a mixture of ethyl 1-(4-phenoxybenzyl)-3-(4-phenoxybenzyloxy)-1H-pyrazole-4-carboxylate (500 mg), 1N sodium hydroxide solution (2 ml), tetrahydrofuran (5 ml), and ethanol (5 ml) was stirred at room temperature for 2 hours, 1N hydrochloric acid (3 ml) was added to the mixture, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous sodium chloride solution, dried (MgSO4), and concentrated. The resulting colorless crystals were collected by filtration to obtain 1-(4-phenoxybenzyl)-3-(4-phenoxybenzyloxy)-1H-pyrazole-4-carboxylic acid (450 mg, yield: 95%). This was recrystallized from acetone-hexane. Melting point: 141–142° C.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with saturated aqueous sodium chloride solution
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. filtrationThe resulting colorless crystals were collected by filtration

Sources & evidence

ORD record
ord-cb305d1dca694258b862d7737d22be3d
Source dataset
uspto-grants-2007_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07179823B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes