Réaction #1929012

Équation de réaction

water

thionyl chloride

4-propylcyclohexanol

DMF

→

1-chloro-4-propylcyclohexane

Solvants

toluene

Conditions de réaction

Traitement

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

Mode opératoire

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