Dimethyl dicarbonate → 2,3,3',4'-Tetramethylbenzophenone

HRID 418890

反応式

HRID 418890 の反応式
[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1B(O)O.[CH3:12][C:13]1[CH:14]=[C:15]([CH:19]=[CH:20][C:21]=1[CH3:22])[C:16](O)=[O:17].C(OC(OC)=O)(OC)=O.C(=O)([O-])[O-].[K+].[K+]>[Pd].O1CCOCC1.O>[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:16]([C:15]1[CH:19]=[CH:20][C:21]([CH3:22])=[C:13]([CH3:12])[CH:14]=1)=[O:17]

参加物

8

反応物 4

HCID 3086Dimethyl dicarbonateHCID 11430Potassium CarbonateHCID 120733,4-Dimethylbenzoic acidHCID 27733952,3-Dimethylphenylboronic acid

生成物 1

HCID 203721182,3,3',4'-Tetramethylbenzophenone収率 42%

試薬・触媒・溶媒 3

HCID 23938Palladium触媒HCID 962Water溶媒HCID 312751,4-Dioxane溶媒2 回

反応条件

温度
80 °C

実験手順

To a 250 ml 3-necked round-bottom flask, 2,3-dimethylphenylboronic acid (3.6 g, 24 mmol), 3,4-dimethylbenzoic acid (3.0 g, 20 mmol), a selected palladium catalyst (0.6 mmol), dimethyl dicarbonate (2.7 g, 30 mmol) and potassium carbonate (6.22 g, 45 mmol) were mixed with 150 ml of dry dioxane. The reaction mixture was heated at 80° C. overnight to become a viscous reaction mixture. 20 ml of water was added to dissolve the heterogeneous reaction mixture, and dioxane was evaporated to dryness. The aqueous solution as extracted with 20 ml of ethyl acetate, dried over anhydrous magnesium sulfate and then evaporated to dryness. The crude product was purified by silica gel column chromatography eluted by hexane/ethyl acetate=20/80 to afford 2.0 g (33%) of the product.

後処理

  1. customwas evaporated to dryness
  2. extractionThe aqueous solution as extracted with 20 ml of ethyl acetate
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customevaporated to dryness
  5. customThe crude product was purified by silica gel column chromatography
  6. washeluted by hexane/ethyl acetate=20/80

出典と根拠

ORDレコード
ord-40f67c7c6ebe4f6fa1f0e5363b4b4569
出典データセット
uspto-grants-2012_01
特許番号
US08093348B1

関連ノート

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