Benzophenone → 3,3-Diphenylacrylonitrile

HRID 469262

Reaction equation

HRID 469262 reaction equation
[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

Participants

4

Reactant 3

HCID 3102BenzophenoneHCID 6342Acetonitrile2×HCID 14797Potassium Hydroxide

Product 1

HCID 2743523,3-DiphenylacrylonitrileYield 73.3%

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-f8097f9a50d0425c96c8f703a9bad69c
Source dataset
uspto-grants-2014_01
Patent number
US08629149B2

Linked notes

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