Reaction #52079

Reaction equation

6-methanesulfonyloxyundecane

lithium chloride

water

→

6-chloroundecane

Yield 97.1%

Solvents

N,N-dimethylformamide

Conditions

Workup

1. 1
   Temperatureunder cooling with ice
2. 2
   TemperatureThe mixture was warmed to 50˜55° C.
3. 3
   ExtractionThe reaction mixture was extracted three times with 150 mL of hexane
4. 4
   Washthe organic layer was sequentially washed with 150 mL of water and 150 mL of a saturated aqueous solution of sodium chloride
5. 5
   Dryingdried over 6 g of anhydrous magnesium sulfate
6. 6
   FiltrationAfter filtering off the anhydrous magnesium sulfate
7. 7
   workup.DISTILLATIONthe solvent was distilled off under reduced pressure

Procedure

Thirty grams (0.12 mol) of 6-methanesulfonyloxyundecane was dissolved in 150 mL of N,N-dimethylformamide and 15.3 g (0.36 mol) of anhydrous lithium chloride was added to the solution under cooling with ice. The mixture was warmed to 50˜55° C. and stirred for 3 hours. Thereafter, the mixture was cooled to 15° C. and 300 mL of cold water was added. The reaction mixture was extracted three times with 150 mL of hexane and the organic layer was sequentially washed with 150 mL of water and 150 mL of a saturated aqueous solution of sodium chloride and thereafter dried over 6 g of anhydrous magnesium sulfate. After filtering off the anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure to give 22.2 g (97.1% in yield) of 6-chloroundecane.

Source