Reaktion #44760

Reaktionsgleichung

water

4-(benzyl)phenol

1-bromo-2-chloroethane

cesium carbonate

→

1-(2-chloroethoxy)-4-(benzyl)benzene

Ausbeute 86.0%

Lösungsmittel

acetonitrile

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturat reflux for 12 hours
2. 2
   TemperaturAfter cooling
3. 3
   ExtraktionThe mixture was extracted with ethyl acetate
4. 4
   WaschenThe organic layer was washed with brine
5. 5
   Trocknendried over sodium sulfate
6. 6
   Einengenconcentrated under reduced pressure

Vorschrift

A solution of 4-(benzyl)phenol (638 mg, 3.46 mmol), 1-bromo-2-chloroethane (2.3 mL, 27.7 mmol) and cesium carbonate (4.5 g, 27.7 mmol) in 35 mL of acetonitrile was heated at reflux for 12 hours. After cooling, water was added. The mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, and concentrated under reduced pressure. Flash chromatography gave 734 mg of 1-(2-chloroethoxy)-4-(benzyl)benzene, 1H NMR (300 MHz, CDCl3) δ 7.29 (dd, 2H), 7.19 (dd, 1H), 7.18 (d, 2H), 7.12 (d, 2H), 6.85 (d, 2H), 4.21 (t, 2H), 3.93 (s, 2H), 3.80 (t, 2H) ppm.

Quelle