Anisole → (4-Methoxyphenyl)(3-methylphenyl)methanone

HRID 228600

Reaction equation

HRID 228600 reaction equation
[C:1]1([O:7][CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:9][C:10]1[CH:11]=[C:12]([CH:16]=[CH:17][CH:18]=1)[C:13](Cl)=[O:14].C(=O)([O-])O.[Na+]>[N+](C)([O-])=O.FC(F)(F)S([O-])(=O)=O.[Sc+3].FC(F)(F)S([O-])(=O)=O.FC(F)(F)S([O-])(=O)=O>[CH3:8][O:7][C:1]1[CH:6]=[CH:5][C:4]([C:13]([C:12]2[CH:16]=[CH:17][CH:18]=[C:10]([CH3:9])[CH:11]=2)=[O:14])=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 7519AnisoleHCID 743753-Methylbenzoyl chlorideHCID 516892Sodium Bicarbonate

Product 1

HCID 12469466(4-Methoxyphenyl)(3-methylphenyl)methanoneYield 56%

Reagents, catalysts & solvents 2

HCID 2734571Scandium(III) triflateCatalystHCID 6375NitromethaneSolvent

Conditions

Temperature
60 °C

Procedure

Commercially available anisole (541 mg) and 3-methylbenzoyl chloride (773 mg) were dissolved in nitromethane (5 ml) to prepare a solution. Scandium trifluoromethanesulfonate (49 mg) was added to the solution, and the mixture was stirred at 60° C. overnight. A saturated aqueous sodium hydrogencarbonate solution was added thereto, and the mixture was extracted with chloroform. The organic layer was washed with saturated brine, was dried over sodium sulfate, and was then concentrated. The residue was subjected to separation and purification by column chromatography on silica gel using hexane-acetone as a solvent to give (4-methoxyphenyl)(3-methylphenyl)methanone (633 mg, yield 56%).

Workup

  1. customto prepare a solution
  2. extractionthe mixture was extracted with chloroform
  3. washThe organic layer was washed with saturated brine
  4. dry with materialwas dried over sodium sulfate
  5. concentrationwas then concentrated
  6. customThe residue was subjected to separation and purification by column chromatography on silica gel

Sources & evidence

ORD record
ord-5f4eec60edfd4bbb9e63354c0a2035da
Source dataset
uspto-grants-2009_07
Patent number
US07560558B2

Linked notes

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