4-Methylbenzophenone → HCID 85301076, compound

HRID 924535Notes

Reaction equation

HRID 924535 reaction equation
[CH3:1][C:2]1[CH:15]=[CH:14][C:5]([C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=O)=[CH:4][CH:3]=1>C1COCC1.Cl[Ti](Cl)(Cl)Cl.[Zn]>[CH3:1][C:2]1[CH:15]=[CH:14][C:5]([C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[C:6]([C:5]2[CH:4]=[CH:3][C:2]([CH3:1])=[CH:15][CH:14]=2)[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 1

HCID 86524-Methylbenzophenone

Product 1

HCID 85301076HCID 85301076, compoundYield 94%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 24193Titanium TetrachlorideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A suspension of 4-methylbenzophenone (1, 3.6 g, 10.0 mmol), TiCl4 (1.9 g, 10.0 mmol), and Zn dust (1.3 g, 20.0 mmol) in dry THF (100 mL) was refluxed for 20 g. Afterward, the reaction mixture was cooled to room temperature and filtered. The filtrate was evaporated and the crude product was purified on a silica-gel column using DCM as eluent. 1,2-Bis(4-methylphenyl)-1,2-diphenylethene was isolated as white solid in 94% yield. 1H NMR (300 MHz, CDCl3), δ (TMS, ppm): 7.11-7.00 (m, 10H), 6.91 (d, 8H), 2.26 (d, 6H). δ (75 MHz, CDCl3) 144.8, 141.6, 141.1, 136.6, 132.0, 131.9, 129.0, 128.2, 126.9, 21.9. m/z (FAB) 360.2 [M+ ]; calc. 360.2.

Workup

  1. temperaturewas refluxed for 20 g
  2. filtrationfiltered
  3. customThe filtrate was evaporated
  4. customthe crude product was purified on a silica-gel column

Sources & evidence

ORD record
ord-afa4d8e34a314576a3ae6710459ae3c9
Source dataset
uspto-grants-2016_03
Patent number
US09279806B2

Reaction notes

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