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

HRID 130647

반응식

HRID 130647 반응식
[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]

참가 물질

8

반응물 4

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

생성물 1

HCID 203721182,3,3',4'-Tetramethylbenzophenone수율 42%

시약·촉매·용매 3

HCID 23938Palladium촉매HCID 962Water용매HCID 312751,4-Dioxane용매2회

반응 조건

온도
80 °C

실험 절차

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 was 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.

후처리

  1. customwas evaporated to dryness
  2. extractionThe aqueous solution was 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

출처 및 근거

ORD 기록
ord-3be3222c0dbc41d1af544c056c2c0c43
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07381849B1

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