Chlorocyclohexane → Tricyclohexylbenzene

HRID 1185987Notes

Reaction equation

HRID 1185987 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

To 20.0 g of benzene, 6.83 g of aluminum chloride was added, cooled by 3° C. and stirred, and 40.4 g of cyclohexyl chloride was slowly added dropwise. After the dropwise addition, the mixture was stirred for 5 hours at room temperature and was poured into ice water. An organic phase was extracted using ethyl acetate and the obtained organic phase was distilled off at reduced pressure at 40° C. After further distilling off at reduced pressure at 170° C., the organic phase was cooled to room temperature, 50 ml of acetone was introduced and recrystallized. The precipitated crystals were filtered off and 14 g of tricyclohexylbenzene was obtained.

Workup

  1. additionAfter the dropwise addition
  2. stirringthe mixture was stirred for 5 hours at room temperature
  3. extractionAn organic phase was extracted
  4. distillationthe obtained organic phase was distilled off at reduced pressure at 40° C
  5. distillationAfter further distilling off at reduced pressure at 170° C.
  6. temperaturethe organic phase was cooled to room temperature
  7. addition50 ml of acetone was introduced
  8. customrecrystallized
  9. filtrationThe precipitated crystals were filtered off

Sources & evidence

ORD record
ord-15212c28defa4df88e6588c79f58b0b5
Source dataset
uspto-grants-2014_03
Patent number
US08673538B2

Reaction notes

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