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

HRID 547869

Reaction equation

HRID 547869 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-4676e307cbee4686bb877e33a0332d5d
Source dataset
uspto-grants-2011_05
Patent number
US07939613B2

Linked notes

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