Toluene → 2,3-Dimesityl-2-butene

HRID 254132

Reaction equation

HRID 254132 reaction equation
[C:1]([C:4]1[C:9]([CH3:10])=[CH:8][C:7]([CH3:11])=[CH:6][C:5]=1[CH3:12])(=O)[CH3:2].[C:13]1([CH3:19])[CH:18]=C[CH:16]=[CH:15][CH:14]=1.[C:20]([O-])([O-])=O.[K+].[K+].O1[CH2:30][CH2:29][CH2:28][CH2:27]1>[Zn].Cl[Ti](Cl)(Cl)Cl>[C:5]1([CH3:12])[CH:6]=[C:7]([CH3:11])[CH:8]=[C:9]([CH3:10])[C:4]=1[C:1](=[C:28]([C:29]1[C:30]([CH3:20])=[CH:18][C:13]([CH3:19])=[CH:14][C:15]=1[CH3:16])[CH3:27])[CH3:2]

Participants

7

Reactant 4

HCID 1140TolueneHCID 8028TetrahydrofuranHCID 11430Potassium CarbonateHCID 15461Ethanone, 1-(2,4,6-trimethylphenyl)-

Product 1

HCID 731774902,3-Dimesityl-2-butene

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 24193Titanium TetrachlorideCatalyst

Procedure

1-acetyl-2,4,6-trimethylbenzene (5 mmol, 832 μL) was added to a suspension of Zn (20 mmol, 1.3 g) in tetrahydrofuran (THF, 10 mL) under N2 immersed in an ice bath followed by a toluene solution of TiCl4 (10 mmol, 10 mL of 1M sol.). The reaction mixture was stirred 2 hour at ice-bath temperature and then refluxed for ca. 18 hours. After the reaction mixture had cooled to ambient, 10% aqueous solution of K2CO3 (ca 30 mL) was added and the solution was extracted twice with ether. Combine extract were washed with brine, dried over MgSO4, filtered and evaporated. Chromatography with hexanes on silica gel afforded 250 mg of pure product.

Workup

  1. customimmersed in an ice bath
  2. temperaturerefluxed for ca. 18 hours
  3. additionwas added
  4. extractionthe solution was extracted twice with ether
  5. extractionCombine extract
  6. washwere washed with brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-0ad780e34bcc4bc39d5b0e9c301749f2
Source dataset
uspto-grants-2011_01
Patent number
US07875408B2

Linked notes

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