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

HRID 924533

Reaction equation

HRID 924533 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)-1,2diphenylethene (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-662b9fadbf904ee0a0e52dc833a62cbb
Source dataset
uspto-grants-2016_03
Patent number
US09279806B2

Linked notes

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