Potassium Cyanide → 4,4'-(1-Oxoethane-1,2-diyl)dibenzonitrile

HRID 654828Notes

Reaction equation

HRID 654828 reaction equation
[C:1]([C:3]1[CH:10]=[CH:9][C:6]([CH:7]=[O:8])=[CH:5][CH:4]=1)#[N:2].[C-:11]#[N:12].[K+]>C(O)C.O>[O:8]=[C:7]([C:6]1[CH:9]=[CH:10][C:3]([C:1]#[N:2])=[CH:4][CH:5]=1)[CH2:1][C:3]1[CH:10]=[CH:9][C:6]([C:11]#[N:12])=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 9032Potassium CyanideHCID 660424-Cyanobenzaldehyde

Product 1

HCID 198864384,4'-(1-Oxoethane-1,2-diyl)dibenzonitrile

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 25 g of p-cyanobenzaldehyde in 50 ml of ethanol was added 5 g of potassium cyanide in 10 ml of water. The mixture was heated at reflux for 1 hr, cooled, and the crystalline product was filtered and washed with cold ethanol. Recrystallization from acetic acid afforded 4.7 g of the part (a) title compound, mp. 209°-215° C.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 1 hr
  3. temperaturecooled
  4. filtrationthe crystalline product was filtered
  5. washwashed with cold ethanol
  6. customRecrystallization from acetic acid

Sources & evidence

ORD record
ord-4f158b3539bd4bea8096b41b5bc6f161
Source dataset
uspto-grants-1992_07
Patent number
US05134150

Reaction notes

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