Chlorocyclohexane → Tricyclohexylbenzene

HRID 926441

Reaction equation

HRID 926441 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, followed by cooling/stirring at 3° C., and 40.4 g of cyclohexyl chloride was slowly added dropwise. After the dropwise addition, the mixture was stirred at room temperature for 5 hours and poured into ice water. The organic layer was extracted with ethyl acetate, and the obtained organic layer was distilled off under reduced pressure at 40° C. After further distillation off under reduced pressure at 170° C., the product was cooled to room temperature, charged into 50 ml of acetone and thereby recrystallized. The crystal precipitated was collected by filtration to obtain 14 g of tricyclohexylbenzene.

Workup

  1. additionAfter the dropwise addition
  2. stirringthe mixture 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. distillationAfter further distillation off under reduced pressure at 170° C.
  6. temperaturethe product was cooled to room temperature
  7. additioncharged into 50 ml of acetone
  8. customrecrystallized
  9. customThe crystal precipitated
  10. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-07539820e33d4892b166061072dcd109
Source dataset
uspto-grants-2016_03
Patent number
US09285679B2

Linked notes

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