Toluene → 1,2,3,4-Tetrahydro-1,1,4,4,6-pentamethylnaphthalene

HRID 266671Notes

Reaction equation

HRID 266671 reaction equation
Cl[C:2]([CH3:10])([CH2:4][CH2:5][C:6](Cl)([CH3:8])[CH3:7])[CH3:3].[Al+3].[Cl-].[Cl-].[Cl-].[C:15]1([CH3:21])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>>[CH3:21][C:15]1[CH:20]=[CH:19][C:18]2[C:6]([CH3:8])([CH3:7])[CH2:5][CH2:4][C:2]([CH3:10])([CH3:3])[C:17]=2[CH:16]=1

Participants

4

Reactant 3

HCID 1140TolueneHCID 80360Hexane, 2,5-dichloro-2,5-dimethyl-HCID 6451240Aluminum(III) Chloride

Product 1

HCID 811871,2,3,4-Tetrahydro-1,1,4,4,6-pentamethylnaphthaleneYield 90%

Procedure

2,5-Dichloro-2,5-dimethylhexane (67.5 g, 0.369 mol) was dissolved in dry toluene (200 ml), and then AlCl3 (4.05 g, 30.4 mmol) was crushed up and added portionwise to the solution. After being left for 2 hours, the reaction mixture was poured into ice/5% HCl and the mixture was extracted with hexane. The organic layer was washed each twice with water, aqueous sodium hydrogen carbonate, and then with water, dried over MgSO4, and the solvent was removed by evaporation. The residue was distilled to give 5,6,7,8-tetrahydro-2,5,5,8,8-pentamethylnaphthalene (70.42 g, yield: 90%). bp 100° C. (solidified at room temperature).

Workup

  1. additionadded portionwise to the solution
  2. extractionthe mixture was extracted with hexane
  3. washThe organic layer was washed each twice with water, aqueous sodium hydrogen carbonate
  4. dry with materialwith water, dried over MgSO4
  5. customthe solvent was removed by evaporation
  6. distillationThe residue was distilled

Sources & evidence

ORD record
ord-761b847cf8e74abd96bbc3c1bb21f911
Source dataset
uspto-grants-1997_07
Patent number
US05652232

Reaction notes

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