Sodium Iodide → 1-(2-Hydroxy-4-methoxyphenyl)-2-(4-methoxyphenyl)ethanone

HRID 1950620Notes

Reaction equation

HRID 1950620 reaction equation
C[O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1[C:11](=[O:21])[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=1.[I-].[Na+].O.O.O.O.O.O.O.[Cl-].[Ce+3].[Cl-].[Cl-].C(OCC)(=O)C>C(#N)C.O>[OH:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1[C:11](=[O:21])[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=1

Participants

7

Reactant 4

HCID 5238Sodium Iodide2×HCID 8857Ethyl AcetateHCID 134271631-(2,4-Dimethoxyphenyl)-2-(4-methoxyphenyl)ethanoneHCID 21585214Cerium trichloride heptahydrate2×

Product 1

HCID 3547791-(2-Hydroxy-4-methoxyphenyl)-2-(4-methoxyphenyl)ethanoneYield 93.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

The title compound was synthesized by referring to Chem. Lett., 2000, (7), 738. To a solution of 1-(2,4-dimethoxyphenyl)-2-(4-methoxyphenyl)ethanone (2.8 g) in acetonitrile (150 ml) were sequentially added sodium iodide (3.0 g) and cerium(III) chloride heptahydrate (5.7 g), and the solution was refluxed for 20 hours and 30 minutes. Sodium iodide (760 mg) and cerium(III) chloride heptahydrate (1.9 g) were added thereto, and the solution was further refluxed for 22 hours 30 minutes. To the reaction solution were added ethyl acetate and water, the solution was filtered through celite pad, extracted with ethyl acetate, then washed with brine, dried over anhydrous magnesium sulfate, and then filtered. The filtrate was adsorbed onto silica gel and purified by silica gel column chromatography (hexane-ethyl acetate system) to provide the title compound (2.5 g).

Workup

  1. customThe title compound was synthesized
  2. temperaturethe solution was refluxed for 20 hours and 30 minutes
  3. temperaturethe solution was further refluxed for 22 hours 30 minutes
  4. filtrationthe solution was filtered through celite pad
  5. extractionextracted with ethyl acetate
  6. washwashed with brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. custompurified by silica gel column chromatography (hexane-ethyl acetate system)

Sources & evidence

ORD record
ord-8ece57c3a37849199ed5c78cfcfb6b63
Source dataset
uspto-grants-2013_03
Patent number
US08399520B2

Reaction notes

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