Citric Acid → HCID 57667884, compound

HRID 2191680Notes

Reaction equation

HRID 2191680 reaction equation
C(O)C.[F:4][C:5]1[CH:28]=[CH:27][C:8]([NH:9][C:10]2[CH:19]=[C:18]([O:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH:17]=[CH:16][C:11]=2[C:12]([O:14]C)=[O:13])=[CH:7][CH:6]=1.[OH-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C(OCC)(=O)C>[F:4][C:5]1[CH:28]=[CH:27][C:8]([NH:9][C:10]2[CH:19]=[C:18]([O:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH:17]=[CH:16][C:11]=2[C:12]([OH:14])=[O:13])=[CH:7][CH:6]=1

Participants

6

Reactant 4

HCID 311Citric AcidHCID 702EthanolHCID 14798Sodium Hydroxide2×HCID 57668007HCID 57668007, compound

Product 1

HCID 57667884HCID 57667884, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

To a suspension of ethanol 3.0 mL of methyl 2-(4-fluoroanilino)-4-phenoxybenzoate 36 mg was added 10% sodium hydroxide aqueous solution 1.0 mL at room temperature, and it was stirred at 60° C. for 1 hour and 30 minutes. After the reaction mixture was cooled to room temperature,10% sodium hydroxide aqueous solution 1.0 mL was added, and it was heated and refluxed for 30 minutes. After the reaction mixture was cooled to room temperature,10% citric acid aqueous solution and ethyl acetate were added to it. The organic layer was separated and collected,dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. Diisopropyl ether and hexane were added to the obtained residue, and insoluble matter was filtrated. The solvent of filtrate was removed under reduced pressure, hexane was added to the residue, and solid matter was filtrated to give 2-(4-fluoroanilino)-4-phenoxybenzoic acid 10 mg of white solid.

Workup

  1. temperatureAfter the reaction mixture was cooled to room temperature
  2. temperatureit was heated
  3. temperaturerefluxed for 30 minutes
  4. temperatureAfter the reaction mixture was cooled to room temperature
  5. customThe organic layer was separated
  6. customthe solvent was removed under reduced pressure
  7. additionDiisopropyl ether and hexane were added to the obtained residue, and insoluble matter
  8. filtrationwas filtrated
  9. customThe solvent of filtrate was removed under reduced pressure, hexane
  10. additionwas added to the residue, and solid matter
  11. filtrationwas filtrated

Sources & evidence

ORD record
ord-3c6eb0349bb44ecd9556010c41f10525
Source dataset
uspto-grants-2012_12
Patent number
US08327467B2

Reaction notes

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