Methanol → 2,2'-(Ethene-1,2-diyl)dibenzonitrile

HRID 463502Notes

Reaction equation

HRID 463502 reaction equation
[C:1]([C:3]1[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=1[CH2:5]Cl)#[N:2].[OH-].[Na+].ClCl.CO>CN(C)C=O>[C:4]1([CH:5]=[CH:5][C:4]2[C:3]([C:1]#[N:2])=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:3]([C:1]#[N:2])=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 14798Sodium HydroxideHCID 24526ChlorineHCID 69152Benzonitrile, 2-(chloromethyl)- (9CI)

Product 1

HCID 543052002,2'-(Ethene-1,2-diyl)dibenzonitrileYield 77.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
20 °C

Procedure

30.4 g (0.2 mole) of o-cyanobenzyl chloride are dissolved in 70 g of dimethylformamide, and 24 g (0.6 mole) of sodium hydroxide powder are added at the same time as nitrogen is passed in. The mixture is stirred at 20° C. for about 6-10 hours until all the organically bound chlorine has reacted, 70 g of methanol are added dropwise, and the precipitate is filtered off with suction at 0° C. and is washed with methanol and then with water until no chlorine ions are detectable in the water from the wash. Drying gives 17.8 g of stilbene-2,2'-dicarbonitrile in the form of white crystals.

Workup

  1. customhas reacted
  2. filtrationthe precipitate is filtered off with suction at 0° C.
  3. washis washed with methanol
  4. customDrying

Sources & evidence

ORD record
ord-2d3edb2858574f698f10dddf1fd967a5
Source dataset
uspto-grants-1985_05
Patent number
US04519953

Reaction notes

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