Reaction #44760

Reaction equation

water

4-(benzyl)phenol

1-bromo-2-chloroethane

cesium carbonate

→

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

Yield 86.0%

Solvents

acetonitrile

Conditions

Workup

1. 1
   Temperatureat reflux for 12 hours
2. 2
   TemperatureAfter cooling
3. 3
   ExtractionThe mixture was extracted with ethyl acetate
4. 4
   WashThe organic layer was washed with brine
5. 5
   Dryingdried over sodium sulfate
6. 6
   Concentrationconcentrated under reduced pressure

Procedure

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.

Source