Styrene → 1-Methoxy-2-(2-phenylethenyl)benzene

HRID 1156247Notes

Reaction equation

HRID 1156247 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][CH:9]=[CH:8][C:4]=1[C:5](Cl)=O.C=[CH:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(N(CCCC)CCCC)CCC>C(=O)(OCC)OCC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:1][O:2][C:3]1[CH:11]=[CH:10][CH:9]=[CH:8][C:4]=1[CH:5]=[CH:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 3

HCID 7501StyreneHCID 7622TributylamineHCID 889692-Methoxybenzoyl chloride

Product 1

HCID 6108741-Methoxy-2-(2-phenylethenyl)benzeneYield 49%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 7766Diethyl CarbonateSolvent

Procedure

The procedure described in Example 1 is followed, except that 17.1 g (0.1 mol) of 2-methoxybenzoyl 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 3 hours at a bath temperature of 140° C., in 100 ml of diethyl carbonate as the solvent, 10.3 g (0.049 mol) of 2-methoxystilbene, corresponding to a yield of 49% of theory, are obtained; melting point 69°-70° C.

Sources & evidence

ORD record
ord-f76551ff6c58471e8fcc075c0b4ef5af
Source dataset
uspto-grants-1982_06
Patent number
US04335055

Reaction notes

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