Styrene → 2-Methylstilbene

HRID 1156246Notes

Reaction equation

HRID 1156246 reaction equation
[C:1]1([CH3:10])[C:2]([C:7](Cl)=O)=[CH:3][CH:4]=[CH:5][CH:6]=1.C=[CH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(N(CCCC)CCCC)CCC>C1(=O)CCCCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:10][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]=[CH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 3

HCID 7501StyreneHCID 7622TributylamineHCID 702762-Methylbenzoyl chloride

Product 1

HCID 6066552-MethylstilbeneYield 55.6%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 7967CyclohexanoneSolvent

Procedure

The procedure described in Example 1 is followed, except that 15.5 g (0.1 mol) of o-toluic acid chloride, 13 g (0.125 mol) of styrene, 23.2 g (0.125 mol) of tri-n-butylamine and 0.225 g (0.001 mol) of palladium acetate are used. After a reaction time of 4 hours at 120° C., in 100 ml of cyclohexanone as the solvent, 10.8 g (0.0556 mol) of 2-methylstilbene, corresponding to a yield of 55.6% of theory, are obtained; melting point 92°-93° C.

Sources & evidence

ORD record
ord-e894506431af428b887f449f45afb4d8
Source dataset
uspto-grants-1982_06
Patent number
US04335055

Reaction notes

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