Citric Acid → HCID 15700705, compound

HRID 384146Notes

Reaction equation

HRID 384146 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[H-].[Na+].[Br:11][CH2:12][CH2:13][CH2:14]Br.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CN(C)C=O>[Br:11][CH2:12][CH2:13][CH2:14][O:8][C:5]1[CH:6]=[CH:7][C:2]([I:1])=[CH:3][CH:4]=1

Participants

6

Reactant 4

HCID 311Citric AcidHCID 80011,3-DibromopropaneHCID 108944-IodophenolHCID 24758Sodium hydride

Product 1

HCID 15700705HCID 15700705, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-iodophenol (1.0 g) in dimethylformamide (10 ml), 273 mg of sodium hydride and 0.603 ml of 1,3-dibromopropane were added under ice-cooling, and the reaction solution was stirred at room temperature for 1 hour. To the reaction solution was added 10% aqueous citric acid, and the mixture was extracted with ethyl acetate. The combined organic layers were washed with a saturated saline solution and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the residue obtained was purified by silica gel column chromatography (eluent: hexane/ethyl acetate (98:2-50/50)) to afford the title compound as a colorless oil.

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe combined organic layers were washed with a saturated saline solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe residue obtained
  7. customwas purified by silica gel column chromatography (eluent: hexane/ethyl acetate (98:2-50/50))

Sources & evidence

ORD record
ord-138cf33a7db742b5ba78393eba41950d
Source dataset
uspto-grants-2013_02
Patent number
US08367708B2

Reaction notes

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