Benzoyl chloride → 3-Phenylprop-2-enenitrile

HRID 1156450Notes

Reaction equation

HRID 1156450 reaction equation
[C:1](#[N:4])[CH:2]=[CH2:3].C(Cl)(=O)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C(N(CCCC)CCCC)CCC>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CC1C=CC(C)=CC=1>[C:1](#[N:4])[CH:2]=[CH:3][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

6

Reactant 3

HCID 7412Benzoyl chlorideHCID 7622TributylamineHCID 7855Acrylonitrile

Product 1

HCID 746673-Phenylprop-2-enenitrileYield 540%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 7809P-XyleneSolvent

Procedure

The procedure described in Example 1 is repeated, except that 3.31 g (0.0625 mol) of acrylonitrile, 7.02 g (0.05 mol) of benzoyl chloride, 11.6 g (0.0625 mol) of tri-n-butylamine, 100 ml of p-xylene and 0.1122 g (0.0005 mol) of palladium acetate are used. After a reaction time of 2 hours at 120° C., 3.47 g (0.27 mol) of cinnamonitrile are obtained, corresponding to a yield of 54% of theory. Boiling point=134°-136° C./17×102Pa.

Sources & evidence

ORD record
ord-dd8e624985df4102b6c11f4fa8efe689
Source dataset
uspto-grants-1982_06
Patent number
US04335054

Reaction notes

Loading…