Benzophenone → 3,3-Diphenylacrylonitrile

HRID 469262

Reaktionsgleichung

Reaktionsgleichung von HRID 469262
[C:1]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+].[C:17](#[N:19])[CH3:18]>>[C:2]1([C:1]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:18][C:17]#[N:19])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

4

Edukt 3

HCID 3102BenzophenoneHCID 6342Acetonitrile2×HCID 14797Potassium Hydroxide

Produkt 1

HCID 2743523,3-DiphenylacrylonitrileAusbeute 73,3 %

Versuchsvorschrift

To a solution of benzophenone (9.1 g, 50 mmol) in acetonitrile (20 mL) was added potassium hydroxide (3.3 g, 50 mmol) in acetonitrile (25 mL). The solution was refluxed for 8 hours. The hot reaction mixture was poured into 100 g crushed ice and then extracted with dichloromethane. The organic extract was washed with water, dried over sodium sulfate, and concentrated in vacuo. The crude material was purified by flash column chromatography (diethyl ether/hexanes) to give 3,3-diphenylacrylonitrile (7.7 g, 73.3%) as an oil.

Aufarbeitung

  1. temperatureThe solution was refluxed for 8 hours
  2. additionThe hot reaction mixture was poured into 100 g
  3. customcrushed ice
  4. extractionextracted with dichloromethane
  5. extractionThe organic extract
  6. washwas washed with water
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated in vacuo
  9. customThe crude material was purified by flash column chromatography (diethyl ether/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-f8097f9a50d0425c96c8f703a9bad69c
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08629149B2

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