Chlorocyclohexane → Tricyclohexylbenzene

HRID 1027348

Reaction equation

HRID 1027348 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[CH:5]1(Cl)[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1>C1C=CC=CC=1>[CH:5]1([C:5]2[C:6]([CH:5]3[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]3)=[C:7]([CH:5]3[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]3)[CH:8]=[CH:9][CH:10]=2)[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1

Participants

4

Reactant 2

HCID 10952ChlorocyclohexaneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 3015433TricyclohexylbenzeneYield 50.7%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
3 °C

Procedure

6.83 g of aluminum chloride was added to 20.0 g of benzene, and the mixture was stirred under cooling at 3° C. Subsequently, 40.4 g of cyclohexyl chloride was slowly added dropwise and after the dropwise addition, the reaction solution was stirred at room temperature for 5 hours and then poured in ice water. The organic layer was extracted with ethyl acetate, and the obtained organic layer was distilled off under reduced pressure at 40° C., further distilled off under reduced pressure at 170° C., then cooled to room temperature and recrystallized by charging 50 ml of acetone thereinto. The precipitated crystals were collected by filtration to obtain 14 g of tricyclohexylbenzene.

Workup

  1. additionafter the dropwise addition
  2. stirringthe reaction solution was stirred at room temperature for 5 hours
  3. extractionThe organic layer was extracted with ethyl acetate
  4. distillationthe obtained organic layer was distilled off under reduced pressure at 40° C.
  5. distillationfurther distilled off under reduced pressure at 170° C.
  6. temperaturecooled to room temperature
  7. customrecrystallized
  8. filtrationThe precipitated crystals were collected by filtration

Sources & evidence

ORD record
ord-a814e97254c744a39b40b1903e1b537c
Source dataset
uspto-grants-2014_05
Patent number
US08735048B2

Linked notes

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