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

HRID 2351850Notes

Reaction equation

HRID 2351850 reaction equation
[C:1]1([CH3:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[C:9]([CH3:17])([CH2:11][CH2:12][C:13](Cl)([CH3:15])[CH3:14])[CH3:10].[Cl-].[Al+3].[Cl-].[Cl-]>O>[CH3:7][C:1]1[CH:6]=[CH:5][C:4]2[C:13]([CH3:15])([CH3:14])[CH2:12][CH2:11][C:9]([CH3:17])([CH3:10])[C:3]=2[CH:2]=1

Participants

5

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 98%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

In a round bottom flask there are introduced 64 ml (600 mmoles) of toluene and 36.6 g (200 mmoles) of 2,5-dichloro-2,5-dimethyl hexane. The reaction mixture is cooled to 0° C. and there are added, by small amounts, 4.1 g (30 mmoles) of aluminum chloride. The reaction mixture is stirred for 1 hour at ambient temperature, poured into water and extracted with CH2Cl2. The organic phase is decanted, dried on magnesium sulfate and evaporated. The resulting oil is purified by distillation. 39.4 g (98%) of 2-methyl-5,6,7,8-tetrahydro-5,5,8,8-tetramethyl naphthalene which boils at 68° C. (under 1 mm of mercury) are obtained.

Workup

  1. extractionextracted with CH2Cl2
  2. customThe organic phase is decanted
  3. customdried on magnesium sulfate
  4. customevaporated
  5. distillationThe resulting oil is purified by distillation

Sources & evidence

ORD record
ord-589e4e9bf490454d858c150ff5117093
Source dataset
uspto-grants-1989_10
Patent number
US04874747

Reaction notes

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