p-Toluenesulfonic acid → 2-(2,2-Dimethylbenzo[d][1,3]dioxol-5-yl)acetonitrile

HRID 468233

反応式

HRID 468233 の反応式
[OH:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]#[N:11])[CH:5]=[CH:6][C:7]=1[OH:8].CO[C:14](OC)([CH3:16])[CH3:15].CC1C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH3:15][C:14]1([CH3:16])[O:8][C:7]2[CH:6]=[CH:5][C:4]([CH2:9][C:10]#[N:11])=[CH:3][C:2]=2[O:1]1

参加物

5

反応物 3

HCID 6101p-Toluenesulfonic acidHCID 64952,2-DimethoxypropaneHCID 109097272-(3,4-Dihydroxyphenyl)acetonitrile

生成物 1

HCID 552677322-(2,2-Dimethylbenzo[d][1,3]dioxol-5-yl)acetonitrile収率 20%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

To a solution of (3,4-dihydroxy-phenyl)-acetonitrile (0.20 g, 1.3 mmol) in toluene (4 mL) was added 2,2-dimethoxy-propane (0.28 g, 2.6 mmol) and TsOH (0.010 g, 0.065 mmol). The mixture was heated at reflux overnight. The reaction mixture was evaporated to remove the solvent and the residue was dissolved in ethyl acetate. The organic layer was washed with NaHCO3 solution, H2O, brine, and dried over Na2SO4. The solvent was evaporated under reduced pressure to give a residue, which was purified by column chromatography on silica gel (petroleum ether/ethyl acetate 10:1) to give 2-(2,2-dimethylbenzo[d][1,3]dioxol-5-yl)acetonitrile (40 mg, 20%). 1H NMR (CDCl3, 400 MHz) δ 6.68-6.71 (m, 3H), 3.64 (s, 2H), 1.67 (s, 6H).

後処理

  1. temperatureThe mixture was heated
  2. temperatureat reflux overnight
  3. customThe reaction mixture was evaporated
  4. customto remove the solvent
  5. dissolutionthe residue was dissolved in ethyl acetate
  6. washThe organic layer was washed with NaHCO3 solution, H2O, brine
  7. dry with materialdried over Na2SO4
  8. customThe solvent was evaporated under reduced pressure
  9. customto give a residue, which
  10. customwas purified by column chromatography on silica gel (petroleum ether/ethyl acetate 10:1)

出典と根拠

ORDレコード
ord-a12bac07e87b47d29c8dc7f96afe787a
出典データセット
uspto-grants-2014_01
特許番号
US08623905B2

関連ノート

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