Methanol → 3,7-Dimethyl-2-phenyl-octa-2,6-diene nitrile

HRID 513976

反応式

HRID 513976 の反応式
[CH3:1][C:2]([CH3:9])=[CH:3][CH2:4][CH2:5][C:6](=O)[CH3:7].[CH2:10]([C:17]#[N:18])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[OH-].[K+].CO>>[CH3:7][C:6]([CH2:5][CH2:4][CH:3]=[C:2]([CH3:9])[CH3:1])=[C:10]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:17]#[N:18]

参加物

5

反応物 4

HCID 887MethanolHCID 8794PhenylacetonitrileHCID 98626-Methyl-5-hepten-2-oneHCID 14797Potassium Hydroxide

生成物 1

HCID 675271983,7-Dimethyl-2-phenyl-octa-2,6-diene nitrile収率 24%

実験手順

To the mixture of 6-methyl-hept-5-en-2-one (90.86 g, 0.72 mol) and benzyl cyanide (46.8 g, 0.40 mol) is added dropwise a 4 N solution of KOH in MeOH (25.0 ml, 0.10 mol). The resulting suspension is heated to reflux during 4.5 h. Then methanol is removed by distillation and the residue is washed with 6 N aq. HCl-solution, then water, sat. aq. NaHCO3-solution and brine. The organic layer is dried over MgSO4, the solvent removed under reduced pressure and the residue distilled twice over a Widmer column to yield 3,7-Dimethyl-2-phenyl-octa-2,6-diene nitrile (21.5 g, 24%, (E/Z) mixture) as a colourless oil (b.p. 122DC/0.1 mbar).

後処理

  1. temperatureThe resulting suspension is heated
  2. temperatureto reflux during 4.5 h
  3. customThen methanol is removed by distillation
  4. washthe residue is washed with 6 N aq. HCl-solution
  5. dry with materialThe organic layer is dried over MgSO4
  6. customthe solvent removed under reduced pressure
  7. distillationthe residue distilled twice over a Widmer column

出典と根拠

ORDレコード
ord-10934ee530284961993b77e722fe1d09
出典データセット
uspto-grants-2015_08
特許番号
US09102899B2

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