Benzoyl chloride → Styrene

HRID 484647Notes

Reaction equation

HRID 484647 reaction equation
[C:1](Cl)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:10](N(C)C)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC=CC=1>[CH2:10]=[CH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:2]1(/[CH:1]=[CH:10]/[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 7412Benzoyl chlorideHCID 7681N,N-Dimethylbenzylamine

Product 2

HCID 7501StyreneYield 55%HCID 638088trans-StilbeneYield 9%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

1.44 ml (12.5 mmols) of benzoyl chloride, 1.88 ml (12.5 mmols) of N-benzyldimethylamine and 0.0281 g (0.125 mmol) of palladium acetate are added to 25 ml of toluene in a pressure apparatus constructed of glass. The apparatus is flushed with ethylene in order to remove the air. Ethylene is then injected at 10 bar and the mixture is stirred for 4 hours at 120° C. 55% of styrene and 9% of trans-stilbene are formed.

Workup

  1. customThe apparatus is flushed with ethylene in order
  2. customto remove the air

Sources & evidence

ORD record
ord-3b4ff9d3a9cb4683841ce19326b808e0
Source dataset
uspto-grants-1985_08
Patent number
US04533505

Reaction notes

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