Benzoyl chloride → (2-Methoxy-4,5-dimethylphenyl)(phenyl)methanone

HRID 228596

Reaktionsgleichung

Reaktionsgleichung von HRID 228596
[CH3:1][C:2]1[CH:3]=[C:4]([O:9][CH3:10])[CH:5]=[CH:6][C:7]=1[CH3:8].Cl([O-])(=O)(=O)=O.[Li+].[C:17](Cl)(=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.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>[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([C:17]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:24])=[C:4]([O:9][CH3:10])[CH:3]=1

Komponenten

7

Edukt 4

HCID 7412Benzoyl chlorideHCID 784113,4-DimethylanisoleHCID 516892Sodium BicarbonateHCID 23665649Lithium perchlorate

Produkt 1

HCID 23078360(2-Methoxy-4,5-dimethylphenyl)(phenyl)methanoneAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 2734571Scandium(III) triflateKatalysatorHCID 6375NitromethaneLösungsmittel

Versuchsvorschrift

Commercially available 3,4-dimethylanisole (409 mg) was dissolved in nitromethane (6 ml) to prepare a solution. Lithium perchlorate (1.9 g) and benzoyl chloride (843 mg) were added to the solution, scandium trifluoromethanesulfonate (148 mg) was then added thereto, and the mixture was stirred at room temperature for 3 days. A saturated aqueous sodium hydrogencarbonate solution was added to the reaction solution, and the mixture was extracted with chloroform. The organic layer was washed with saturated brine, was dried over sodium sulfate and was concentrated. The residue was subjected to separation and purification by column chromatography on silica gel using hexane/ethyl acetate as a solvent to give (4,5-dimethyl-2-methoxyphenyl)(phenyl)methanone (667 mg, yield 93%).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-802b722db74e4c3998754ed0872a693d
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07560558B2

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