4-Methoxybenzophenone → 1,1'-[1,2-Bis(4-methoxyphenyl)ethene-1,2-diyl]dibenzene

HRID 1190768Notes

Reaction equation

HRID 1190768 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=O)[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:5][CH:4]=1>C1COCC1.[Zn]>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[C:9]([C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=2)[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)=[CH:5][CH:4]=1

Participants

4

Reactant 1

HCID 691464-Methoxybenzophenone

Product 1

HCID 665911621,1'-[1,2-Bis(4-methoxyphenyl)ethene-1,2-diyl]dibenzeneYield 91%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A suspension of p-methoxybenzophenone (1.06 g, 5.0 mmol), 1.34 equiv of TiCl3/AlCl3 (5.81 g, 6.7 mmol), and 25 equiv of Zn dust (8.01 g, 122.0 mmol) in 100 ml of dry THF was refluxed for 20 h. The reaction mixture was cooled to room temperature and filtered. The filtrates were evaporated and the crude product was purified by a silica gel column using hexane as eluent. 1,2-Bis(4-methoxyphenyl)-1,2-diphenylethene (TPE-OMe) was isolated in 91% yield.

Workup

  1. temperaturewas refluxed for 20 h
  2. filtrationfiltered
  3. customThe filtrates were evaporated
  4. customthe crude product was purified by a silica gel column

Sources & evidence

ORD record
ord-9ceb9726d28b44ab93a78578e7209904
Source dataset
uspto-grants-2014_03
Patent number
US08679738B2

Reaction notes

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