Reaktion #46205

Reaktionsgleichung

(3,4-dihydroxy-phenyl)-acetonitrile

2,2-dimethoxy-propane

TsOH

→

2-(2,2-dimethylbenzo[d][1,3]dioxol-5-yl)acetonitrile

Ausbeute 20.0%

Lösungsmittel

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe mixture was heated
2. 2
   Temperaturat reflux overnight
3. 3
   SonstigeThe reaction mixture was evaporated
4. 4
   Sonstigeto remove the solvent
5. 5
   workup.DISSOLUTIONthe residue was dissolved in ethyl acetate
6. 6
   WaschenThe organic layer was washed with NaHCO3 solution, H2O, brine
7. 7
   Trocknendried over Na2SO4
8. 8
   SonstigeThe solvent was evaporated under reduced pressure
9. 9
   Sonstigeto give a residue, which
10. 10
    Sonstigewas purified by column chromatography on silica gel (Petroleum Ether/EtOAc 10:1)

Vorschrift

To a solution of (3,4-dihydroxy-phenyl)-acetonitrile (0.2 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/EtOAc 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).

Quelle