Chlorocyclohexane → Tricyclohexylbenzene

HRID 1530156Notes

Reaction equation

HRID 1530156 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

Aluminum chloride (6.83 g) was added to 20.0 g of benzene, and the mixture was cooled with stirring at 3° C. Thereto, 40.4 g of cyclohexyl chloride was gradually added dropwise. 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. and further distilled off under reduced pressure at 170° C. The residue was cooled, to room temperature, and 50 ml of acetone was added thereto for recrystallization. The precipitated crystal was collected by filtration to obtain 14 g of tricyclohexylbenzene.

Workup

  1. temperaturethe mixture was cooled
  2. additionAfter the dropwise addition
  3. stirringthe reaction solution was stirred at room temperature for 5 hours
  4. extractionThe organic layer was extracted with ethyl acetate
  5. distillationthe obtained organic layer was distilled off under reduced pressure at 40° C.
  6. distillationfurther distilled off under reduced pressure at 170° C
  7. temperatureThe residue was cooled, to room temperature
  8. addition50 ml of acetone was added
  9. customfor recrystallization
  10. filtrationThe precipitated crystal was collected by filtration

Sources & evidence

ORD record
ord-57c4044c53b149dca6e12b2b77b51d97
Source dataset
uspto-grants-2015_07
Patent number
US09090722B2

Reaction notes

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