Styrene → 3,4,5-Trimethoxystilbene

HRID 1156251Notes

Reaction equation

HRID 1156251 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([O:14][CH3:15])[C:11]=1[O:12][CH3:13])[C:6](Cl)=O.C=[CH:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(N(C(C)C)C(C)C)C>C1(=O)CCCCC1.C/C(/[O-])=C/C(C)=O.C/C(/[O-])=C/C(C)=O.[Pd+2]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:6]=[CH:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:9]=[C:10]([O:14][CH3:15])[C:11]=1[O:12][CH3:13]

Participants

6

Reactant 3

HCID 7501StyreneHCID 78282Benzoyl chloride, 3,4,5-trimethoxy-HCID 81531Diisopropylethylamine

Product 1

HCID 3680813,4,5-TrimethoxystilbeneYield 17.5%

Reagents, catalysts & solvents 2

HCID 5486778Palladium acetylacetonateCatalystHCID 7967CyclohexanoneSolvent

Procedure

The procedure described in Example 1 is followed, except that 23.07 g (0.1 mol) of 3,4,5-trimethoxybenzoyl chloride, 13.02 g (0.125 mol) of styrene, 12.93 g (0.125 mol) of ethyl diisopropylamine and 0.3046 g (0.001 mol) of bis-(acetylacetonato)-palladium(II) are used. After a reaction time of 3 hours at 130° C., in 50 ml of cyclohexanone as the solvent, 4.7 g (0.0175 mol) of 3,4,5-trimethoxystilbene, corresponding to a yield of 17.5% of theory, are obtained in the form of white needles; melting point 108° C.

Sources & evidence

ORD record
ord-60d5a44ed2e04dfdbd6cea8e40a2e2ea
Source dataset
uspto-grants-1982_06
Patent number
US04335055

Reaction notes

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