Water → 1-Chloro-4-propylcyclohexane

HRID 1841830Notes

Reaction equation

HRID 1841830 reaction equation
[CH2:1]([CH:4]1[CH2:9][CH2:8][CH:7](O)[CH2:6][CH2:5]1)[CH2:2][CH3:3].CN(C=O)C.S(Cl)([Cl:18])=O.O>C1(C)C=CC=CC=1>[Cl:18][CH:7]1[CH2:8][CH2:9][CH:4]([CH2:1][CH2:2][CH3:3])[CH2:5][CH2:6]1

Participants

6

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 27750944-Propylcyclohexanol

Product 1

HCID 199612711-Chloro-4-propylcyclohexane

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

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.

Workup

  1. temperaturethe mixture is heated to reflux
  2. temperatureis heated for a further 4 h
  3. temperatureAfter cooling
  4. customthe organic phase is separated off
  5. extractionThe aqueous phase is extracted with toluene
  6. washthe combined organic phases are washed with water and saturated sodium chloride solution
  7. customThe solution is dried
  8. concentrationconcentrated to dryness
  9. customThe crude product is purified by column chromatography (SiO2, n-heptane)

Sources & evidence

ORD record
ord-56570fad56e6459090b2728b42118661
Source dataset
uspto-grants-2015_02
Patent number
US08945420B2

Reaction notes

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