Anisole → 4-t-Butylphenyl 4-methoxyphenyl ketone

HRID 1857119Notes

Reaction equation

HRID 1857119 reaction equation
[C:1]1([O:7][CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:9]([C:13]1[CH:21]=[CH:20][C:16]([C:17](Cl)=[O:18])=[CH:15][CH:14]=1)([CH3:12])([CH3:11])[CH3:10]>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>[CH3:8][O:7][C:1]1[CH:6]=[CH:5][C:4]([C:17]([C:16]2[CH:20]=[CH:21][C:13]([C:9]([CH3:12])([CH3:11])[CH3:10])=[CH:14][CH:15]=2)=[O:18])=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 7519AnisoleHCID 743724-tert-Butylbenzoyl chloride

Product 1

HCID 101992554-t-Butylphenyl 4-methoxyphenyl ketoneYield 64.3%

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 4-t-butylbenzoyl chloride (983 mg) and commercially available scandium(III) trifluoromethanesulfonate (492 mg), and the admixture was stirred at 60° C. for 21 hours. The reaction mixture was partitioned between water and chloroform, and the chloroform layer was then 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 862 mg of the title compound (yield: 64%).

Workup

  1. customThe reaction mixture was partitioned between water and chloroform
  2. dry with materialthe chloroform layer was then 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-2f2032fb655a4df08f48e84c9dab83f9
Source dataset
uspto-grants-2000_11
Patent number
US06143764

Reaction notes

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