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

HRID 468233

Reaktionsgleichung

Reaktionsgleichung von HRID 468233
[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

Komponenten

5

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-a12bac07e87b47d29c8dc7f96afe787a
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08623905B2

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