Reaction #1929012

Reaction equation

water

thionyl chloride

4-propylcyclohexanol

DMF

→

1-chloro-4-propylcyclohexane

Solvents

toluene

Conditions

Workup

1. 1
   Temperaturethe mixture is heated to reflux
2. 2
   Temperatureis heated for a further 4 h
3. 3
   TemperatureAfter cooling
4. 4
   Otherthe organic phase is separated off
5. 5
   ExtractionThe aqueous phase is extracted with toluene
6. 6
   Washthe combined organic phases are washed with water and saturated sodium chloride solution
7. 7
   OtherThe solution is dried
8. 8
   Concentrationconcentrated to dryness
9. 9
   OtherThe crude product is purified by column chromatography (SiO2, n-heptane)

Procedure

100.0 g (0.70 mol) of 4-propylcyclohexanol are initially introduced in 1200 ml of toluene together with 2.7 ml of DMF, and the mixture is heated to reflux. 255 ml (3.52 mol) of thionyl chloride are carefully metered in, and the batch is heated for a further 4 h. After cooling, the mixture is added to water, and the organic phase is separated off. The aqueous phase is extracted with toluene, and the combined organic phases are washed with water and saturated sodium chloride solution. The solution is dried using sodium sulfate and concentrated to dryness. The crude product is purified by column chromatography (SiO2, n-heptane), giving 1-chloro-4-propylcyclohexane as a colourless liquid.

Source