Citric Acid → HCID 23159872, compound

HRID 2110877Notes

Reaction equation

HRID 2110877 reaction equation
[CH3:1][N:2]1[C:6]([CH3:7])=[C:5]([C:8]2[CH:9]=[C:10]([CH:25]=[CH:26][CH:27]=2)[CH2:11][O:12][C:13]2[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][C:21]([O:23]C)=[O:22])=[CH:15][CH:14]=2)[C:4]([CH3:28])=[N:3]1.[OH-].[Na+].O.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CO.O1CCCC1>[CH3:1][N:2]1[C:6]([CH3:7])=[C:5]([C:8]2[CH:9]=[C:10]([CH:25]=[CH:26][CH:27]=2)[CH2:11][O:12][C:13]2[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][C:21]([OH:23])=[O:22])=[CH:15][CH:14]=2)[C:4]([CH3:28])=[N:3]1

Participants

7

Reactant 4

HCID 311Citric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 23159931HCID 23159931, compound

Product 1

HCID 23159872HCID 23159872, compoundYield 100.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixed solution of methyl 3-(4-{[3-(1,3,5-trimethyl-1H-pyrazol-4-yl)benzyl]oxy}phenyl)propanoate (0.406 g, 1.07 mmol) in methanol (5 mL) and tetrahydrofuran (5 mL) was added 2 M aqueous sodium hydroxide solution (1.5 mL), and the mixture was stirred at room temperature for 20 hr. Water was added to the reaction mixture, and the mixture was neutralized with 10% aqueous citric acid solution and extracted with ethyl acetate. The extract washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was recrystallized from ethyl acetate-hexane to give the title compound (0.391 g, quantitative) as colorless needle crystals. MS: m/z 365 (MH+).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-6d44130d33cc49c28d97897ac0aebe0f
Source dataset
uspto-grants-2009_04
Patent number
US07517910B2

Reaction notes

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