Toluene → 2,3-Dimesityl-2-butene

HRID 254132

反応式

HRID 254132 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

HCID 731774902,3-Dimesityl-2-butene

試薬・触媒・溶媒 2

HCID 23994Zinc触媒HCID 24193Titanium Tetrachloride触媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-0ad780e34bcc4bc39d5b0e9c301749f2
出典データセット
uspto-grants-2011_01
特許番号
US07875408B2

関連ノート

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