Citric Acid → HCID 23157653, compound

HRID 508045Notes

Reaction equation

HRID 508045 reaction equation
[CH2:1]([O:3][CH2:4][CH2:5][O:6][C:7]1[CH:12]=[C:11]([CH3:13])[C:10]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([CH2:20][NH:21][C:22]3[CH:34]=[CH:33][C:25]([O:26][CH2:27][C:28]([O:30]CC)=[O:29])=[CH:24][CH:23]=3)[CH:15]=2)=[C:9]([CH3:35])[CH:8]=1)[CH3:2].[OH-].[K+].O.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CO.O1CCCC1>[CH2:1]([O:3][CH2:4][CH2:5][O:6][C:7]1[CH:8]=[C:9]([CH3:35])[C:10]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([CH2:20][NH:21][C:22]3[CH:23]=[CH:24][C:25]([O:26][CH2:27][C:28]([OH:30])=[O:29])=[CH:33][CH:34]=3)[CH:15]=2)=[C:11]([CH3:13])[CH:12]=1)[CH3:2]

Participants

7

Reactant 4

HCID 311Citric AcidHCID 962WaterHCID 14797Potassium HydroxideHCID 59434120HCID 59434120, compound

Product 1

HCID 23157653HCID 23157653, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl [4-({[4′-(2-ethoxyethoxy)-2′,6′-dimethylbiphenyl-3-yl]methyl}amino)phenoxy]acetate (0.37 g, 0.77 mmol) in a mixture of methanol (10 mL) and tetrahydrofuran (10 mL) was added an aqueous solution (5 mL) of potassium hydroxide (0.26 g, 3.94 mmol), and the mixture was stirred at room temperature for 18 hr. Water was added to the reaction mixture, and the mixture was weakly acidified with 10% aqueous citric acid solution and extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained crystals were washed with diethyl ether-hexane to give the title compound as colorless prism crystals. yield 91%.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. washThe obtained crystals were washed with diethyl ether-hexane

Sources & evidence

ORD record
ord-a2ecd3f3d90b4adab9d25bf4476e658f
Source dataset
uspto-grants-2010_08
Patent number
US07786165B2

Reaction notes

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