Reaction #1702077

Reaction equation

diethylether

2-(4-chlorophenyl)ethanol

Dess-Martin periodinane

→

desired compound

Yield 42.2%

2-(4-chlorophenyl)acetaldehyde

Yield 42.2%

Solvents

dichloromethane

Conditions

Workup

1. 1
   Washthe resulting mixture was washed with a 1:1 solution (150 ml) of sodium carbonate (aqueous saturated) and sodium thiosulfate (aqueous saturated)
2. 2
   DryingThe organic phase was then dried over sodium sulfate
3. 3
   Otherevaporated

Procedure

To a solution of 2-(4-chlorophenyl)ethanol (2.00 g, 12.77 mmol) in dichloromethane (100 ml) was added Dess-Martin periodinane (8.12 g, 19.16 mmol) and the mixture was stirred at room temperature over weekend. Then was added diethylether (150 ml) and the resulting mixture was washed with a 1:1 solution (150 ml) of sodium carbonate (aqueous saturated) and sodium thiosulfate (aqueous saturated) and then with sodium bicarbonate (aqueous saturated) and finally with brine. The organic phase was then dried over sodium sulfate and evaporated. Silica gel flash chromatography (pentan/ethylacetate:9/1) afforded the desired compound (0.834 g, 42%) as a white solid.

Source