O-Xylene → 1,1,4,4,6,7-Hexamethyl-1,2,3,4-tetrahydronaphthalene

HRID 277180

Reaction equation

HRID 277180 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].Cl[C:6]([CH3:14])([CH2:8][CH2:9][C:10](Cl)([CH3:12])[CH3:11])[CH3:7].[C:15]1([CH3:22])[C:16]([CH3:21])=[CH:17][CH:18]=[CH:19][CH:20]=1>>[CH3:22][C:15]1[C:16]([CH3:21])=[CH:17][C:18]2[C:10]([CH3:12])([CH3:11])[CH2:9][CH2:8][C:6]([CH3:14])([CH3:7])[C:19]=2[CH:20]=1

Participants

4

Reactant 3

HCID 7237O-XyleneHCID 80360Hexane, 2,5-dichloro-2,5-dimethyl-HCID 6451240Aluminum(III) Chloride

Product 1

HCID 2276411,1,4,4,6,7-Hexamethyl-1,2,3,4-tetrahydronaphthalene

Procedure

7 g of aluminum chloride was added by portions to 200 ml solution of 50 g 2,5-dichloro-2,5-dimethylhexane in orthoxylene at 0° C. under stirring. After the mixture was stirred at the same temperature for 15 minutes, it was poured into ice-cold water and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and then evaporated to give 60 g of 2,3,5,5,8,8-hexamethyl-5,6,7,8-tetrahydronaphthalene as a brown oil.

Workup

  1. stirringAfter the mixture was stirred at the same temperature for 15 minutes
  2. additionit was poured into ice-cold water
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-776ba37bdddb44b9bc5c5baf68b6c105
Source dataset
uspto-grants-2002_03
Patent number
US06355669B1

Linked notes

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