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

HRID 228596
Notes
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Reaction equation

HRID 228596 reaction equation
[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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 2734571
Scandium(III) triflate
Catalyst
HCID 6375NitromethaneSolvent

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-802b722db74e4c3998754ed0872a693d
Source dataset
uspto-grants-2009_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07560558B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes