Styrene → 1,4-Diphenyl-1,3-butadiene

HRID 1156244Notes

Reaction equation

HRID 1156244 reaction equation
[CH2:1](Cl)[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C=[CH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(N(CCCC)CCCC)CCC>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.ClC1C=CC=CC=1>[C:4]1([CH:3]=[CH:2][CH:1]=[CH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 7501StyreneHCID 7622TributylamineHCID 94242Benzene, (3-chloro-1-propenyl)-

Product 1

HCID 134521,4-Diphenyl-1,3-butadieneYield 27.7%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 7964ChlorobenzeneSolvent

Procedure

The procedure described in Example 1 is followed, except that 16.7 g (0.1 mol) of cinnamyl chloride, 13.0 g (0.125 mol) of styrene, 23.3 g (0.125 mol) of tri-n-butylamine, 100 ml of chlorobenzene and 0.225 g (0.001 mol) of palladium acetate are used. After a reaction time of 5 hours at a bath temperature of 140° C., 5.7 g (0.0277 mol) of 1,4-diphenyl-1,3-butadiene, corresponding to a yield of 27.7% of theory, are obtained; melting point 150°-152° C.

Sources & evidence

ORD record
ord-cae6ce65874942e6b61ce420fb9fd0a9
Source dataset
uspto-grants-1982_06
Patent number
US04335055

Reaction notes

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