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

HRID 228600

反応式

HRID 228600 の反応式
[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

参加物

6

反応物 3

HCID 7519AnisoleHCID 743753-Methylbenzoyl chlorideHCID 516892Sodium Bicarbonate

生成物 1

HCID 12469466(4-Methoxyphenyl)(3-methylphenyl)methanone収率 56%

試薬・触媒・溶媒 2

HCID 2734571Scandium(III) triflate触媒HCID 6375Nitromethane溶媒

反応条件

温度
60 °C

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-5f4eec60edfd4bbb9e63354c0a2035da
出典データセット
uspto-grants-2009_07
特許番号
US07560558B2

関連ノート

読み込み中…