Benzoyl chloride → Stilbene

HRID 1156257Notes

Reaction equation

HRID 1156257 reaction equation
[C:1](Cl)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C=[CH:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(N(C)C)C1C=CC=CC=1>CC1C=CC(C)=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:2]1([CH:1]=[CH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 7412Benzoyl chlorideHCID 7501StyreneHCID 7681N,N-Dimethylbenzylamine

Product 1

HCID 11502StilbeneYield 72.6%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 7809P-XyleneSolvent

Procedure

1.12 ml (0.005 millimol) of palladium acetate, 7.04 g (50 millimols) of benzoyl chloride, 5.22 g (50 millimols) of styrene and 6.76 g (50 millimols) of N-benzyldimethylamine in 100 ml of p-xylene are stirred for 11.5 hours at 130° C. 6.54 g (63% of theory) of stilbene are obtained. This corresponds to 6,300 mols of stilbene per mol of catalyst.

Sources & evidence

ORD record
ord-a4efb30737f4415ea207a25590d0202e
Source dataset
uspto-grants-1982_06
Patent number
US04335055

Reaction notes

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