Chlorocyclohexane → Tricyclohexylbenzene

HRID 1509373Notes

Reaction equation

HRID 1509373 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

First, 6.83 g of aluminum chloride was added to 20.0 g of benzene, and agitated while cooling at 3° C. Then, 40.4 g of cyclohexyl chloride was slowly dropped thereinto. After the completion of the dropping, the mixture was agitated at room temperature for five hours and poured into ice water. The organic phase was extracted with ethyl acetate, and the obtained, organic phase was subjected to vacuum distillation at 40° C. Further, vacuum distillation was performed at 170° C., and the product was cooled to room temperature. Thereafter, 50 ml of acetone was placed thereinto, and recrystallization was carried out. The resultant crystal was collected by filtration. Thus, 14 g of tricyclohexylbenzene was obtained.

Workup

  1. stirringAfter the completion of the dropping, the mixture was agitated at room temperature for five hours
  2. extractionThe organic phase was extracted with ethyl acetate
  3. distillationthe obtained, organic phase was subjected to vacuum distillation at 40° C
  4. distillationFurther, vacuum distillation
  5. customwas performed at 170° C.
  6. temperaturethe product was cooled to room temperature
  7. customrecrystallization
  8. filtrationThe resultant crystal was collected by filtration

Sources & evidence

ORD record
ord-f5730cd145cd472990cbe52166e95ab4
Source dataset
uspto-grants-2015_12
Patent number
US09223208B2

Reaction notes

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