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

HRID 1857200Notes

Reaction equation

HRID 1857200 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]>FC(F)(F)S([O-])(=O)=O.[Sc+3].FC(F)(F)S([O-])(=O)=O.FC(F)(F)S([O-])(=O)=O.[N+](C)([O-])=O>[CH3:9][C:10]1[CH:11]=[C:12]([C:13]([C:4]2[CH:5]=[CH:6][C:1]([O:7][CH3:8])=[CH:2][CH:3]=2)=[O:14])[CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 2

HCID 7519AnisoleHCID 743753-Methylbenzoyl chloride

Product 1

HCID 12469466(4-Methoxyphenyl)(3-methylphenyl)methanoneYield 56.1%

Reagents, catalysts & solvents 2

HCID 2734571Scandium(III) triflateCatalystHCID 6375NitromethaneSolvent

Conditions

Temperature
60 °C

Procedure

To commercially available nitromethane (5 ml) were added commercially available anisole (541 mg), commercially available 3-methylbenzoyl chloride (773 mg) and commercially available scandium(III) trifluoromethanesulfonate (49 mg), and the admixture was stirred at 60° C. overnight. The reaction mixture was partitioned between water and chloroform, and the chloroform layer was dried with anhydrous magnesium sulfate. After removing the solvent by reduced-pressure distillation, the resulting residue was purified by column chromatography on silica gel eluting with hexane/acetone to obtain 635 mg of the title compound (yield: 56%).

Workup

  1. customThe reaction mixture was partitioned between water and chloroform
  2. dry with materialthe chloroform layer was dried with anhydrous magnesium sulfate
  3. customAfter removing the solvent
  4. distillationby reduced-pressure distillation
  5. customthe resulting residue was purified by column chromatography on silica gel eluting with hexane/acetone

Sources & evidence

ORD record
ord-eb73647c79044c208f4ca46bdaa3da81
Source dataset
uspto-grants-2000_11
Patent number
US06143764

Reaction notes

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