Reaction #927236

Reaction equation

7-octynyl-p-toluenesulfonate

sodium iodide

→

8-iodo-1-octyne

Yield 94.2%

Solvents

acetone

Conditions

Workup

1. 1
   Otherto react for four hours
2. 2
   Temperatureunder reflux
3. 3
   TemperatureAfter cooling
4. 4
   Otherthe precipitates were removed by filtration
5. 5
   Concentrationthe filtrate was concentrated
6. 6
   OtherThe resulting residue was purified by silica gel column chromatography (eluent; hexane)

Procedure

A mixture of 7-octynyl-p-toluenesulfonate (18.3 g, 65.2 mmol), sodium iodide (9.77 g, 65.2 mmol) and acetone (91 ml) was allowed to react for four hours under reflux. After cooling, the precipitates were removed by filtration, and the filtrate was concentrated. The resulting residue was purified by silica gel column chromatography (eluent; hexane) to afford 14.5 g of 8-iodo-1-octyne (yield; 94.2%).

Source