Styrene → 4-[(E)-2-Phenylethenyl]benzonitrile

HRID 1156250Notes

Reaction equation

HRID 1156250 reaction equation
[C:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7](Cl)=O)=[CH:5][CH:4]=1)#[N:2].C=[CH:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(N(CCCCCCCC)CCCCCCCC)CCCCCCC>C(OCC)(=O)CCC>[C:1]([C:3]1[CH:11]=[CH:10][C:6]([CH:7]=[CH:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:5][CH:4]=1)#[N:2]

Participants

5

Reactant 3

HCID 7501StyreneHCID 14227TrioctylamineHCID 801724-Cyanobenzoyl chloride

Product 1

HCID 6096084-[(E)-2-Phenylethenyl]benzonitrileYield 26.8%

Reagents, catalysts & solvents 1

HCID 7762Ethyl butyrateSolvent

Procedure

The procedure described in Example 1 is followed, except that 16.55 g (0.1 mol) of 4-cyanobenzoyl chloride, 13.02 g (0.125 mol) of styrene, 35.37 g (0.1 mol) of tri-n-octylamine, 50 ml of ethyl butyrate as the solvent and 0.0575 g (0.0001 mol) of bis-(dibenzylideneacetone)-palladium(O) are used. After a reaction time of 2 hours at 100° C., 5.5 g (0.0268 mol) of 4-cyanostilbene, corresponding to a yield of 26.8% of theory, are obtained; melting point 119° C.

Sources & evidence

ORD record
ord-37c9304ae22a4433bf1742a77a853d06
Source dataset
uspto-grants-1982_06
Patent number
US04335055

Reaction notes

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