Reaktion #92505

Reaktionsgleichung

ethylene glycol

3-acetylbenzonitrile

p-TSA

→

19

Ausbeute 76.0%

3-(2-Methyl-1, 3-dioxolan-2-yl)benzonitrile

Ausbeute 76.0%

Lösungsmittel

benzene

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe benzene was removed under reduced pressure
2. 2
   Sonstigethe residue was purified by column chromatography

Vorschrift

To the mixture of ethylene glycol (0.22 mL, 4 mmol), 3-acetylbenzonitrile 18 (300 mg, 2.04 mmol) and benzene (10 mL) in a Dean-Stark apparatus was added a catalytic amount of p-TSA (0.1 equiv). The reaction mixture was heated at 110° C. for 4 h. The benzene was removed under reduced pressure and the residue was purified by column chromatography using ethylacetate-hexane as an eluent to give 19 (293 mg, 76%). 1H NMR (CDCl3, 400 MHz) δ 2.62 (s, 4H), 7.59 (t, J=7.6 Hz, 1H), 7.82 (d, J=7.6 Hz, 1H)), 8.15 (d, J=8 Hz, 1H), 8.21 (s, 1H).

Quelle