Hydrochloric Acid → HCID 22930700, compound

HRID 1295273Notes

Reaction equation

HRID 1295273 reaction equation
[CH2:1]([O:8][C:9]1[CH:13]=[C:12]([C:14]([O:16]CC2C=CC=CC=2)=[O:15])[N:11]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].O1CCCC1.Cl>C(O)C>[CH2:1]([O:8][C:9]1[CH:13]=[C:12]([C:14]([OH:16])=[O:15])[N:11]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[N:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 22930777HCID 22930777, compound

Product 1

HCID 22930700HCID 22930700, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of benzyl 3-benzyloxy-1-phenyl-1H-pyrazole-5-carboxylate (50.88 g), 1N aqueous sodium hydroxide solution (200 ml), tetrahydrofuran (200 ml) and ethanol (200 ml) was refluxed at room temperature for 5 hrs. 1N Hydrochloric acid (200 ml) was added and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. The obtained colorless crystals were collected by filtration to give 3-benzyloxy-1-phenyl-1H-pyrazole-5-carboxylic acid (36.91 g, yield 95%), which was then recrystallized from acetone-isopropyl ether. melting point: 163–164° C.

Workup

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

Sources & evidence

ORD record
ord-1cc4649d58d140c699c53fbb2f56b95e
Source dataset
uspto-grants-2007_07
Patent number
US07241785B2

Reaction notes

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