반응 #307076

반응 방정식

3-formyl-benzonitrile

ethylene glycol

→

title compound

수율 74.9%

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

수율 74.9%

용매

toluene

반응 조건

후처리

1. 1
   온도the mixture was heated
2. 2
   온도to reflux in a Dean-Stark apparatus overnight
3. 3
   농축The toluene was concentrated
4. 4
   기타the reaction mixture purified by flash chromatography (EtOAc/cHex)

실험 절차

To a solution of 3-formyl-benzonitrile (2 g, 15.25 mmol, 1 eq) in dry toluene (30 mL), paratoluenesulfonic acid (262 mg, 1.5 mmol, 0.1 eq) and ethylene glycol (12.8 mL, 228 mmol, 15 eq) were added and the mixture was heated to reflux in a Dean-Stark apparatus overnight. The toluene was concentrated and the reaction mixture purified by flash chromatography (EtOAc/cHex) to afford the title compound as a colorless liquid (2000 mg, 74%). 1H NMR: (CDCl3, 300 MHz) δ 7.78 (m, 1H), 7.69 (m, 1H), 7.64 (m, 1H), 7.48 (t, J=7.7 Hz, 1H), 5.81 (s, 1H), 4.08 (m, 4H). HPLC (Method A) Rt: 2.45 min (purity: 92.1%).

출처