Chlorocyclohexane → Tricyclohexylbenzene

HRID 2035324Notes

Reaction equation

HRID 2035324 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 (6.38 g) was added to 20.0 g of benzene, followed by stirring under cooling at 3° C., and 40.4 g of cyclohexyl chloride was slowly added dropwise thereto. After the dropwise addition, the resultant was stirred at room temperature for 5 hours, and the obtained reaction solution was added to ice water. The organic layer was extracted by using ethyl acetate, and the obtained organic layer was removed by distillation at 40° C. under reduced pressure. The resultant was further removed by distillation at 170° C. under reduced pressure and then cooled to room temperature, and 50 ml of acetone was added thereto to cause recrystallization. The precipitated crystals were collected through filtering, thereby obtaining 14 g of tricyclohexylbenzene.

Workup

  1. additionAfter the dropwise addition
  2. stirringthe resultant was stirred at room temperature for 5 hours
  3. customthe obtained reaction solution
  4. extractionThe organic layer was extracted
  5. customthe obtained organic layer was removed by distillation at 40° C. under reduced pressure
  6. customThe resultant was further removed by distillation at 170° C. under reduced pressure
  7. temperaturecooled to room temperature
  8. addition50 ml of acetone was added
  9. customrecrystallization
  10. customThe precipitated crystals were collected
  11. filtrationthrough filtering

Sources & evidence

ORD record
ord-21951efda33b4875984a232e3799e524
Source dataset
uspto-grants-2013_11
Patent number
US08574814B2

Reaction notes

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