Water → 1,2,3,3,6,6-Hexamethylcyclohex-1-ene

HRID 2290504Notes

Reaction equation

HRID 2290504 reaction equation
O[C:2]1([CH3:13])[CH:7]([CH3:8])[C:6]([CH3:10])([CH3:9])[CH2:5][CH2:4][C:3]1([CH3:12])[CH3:11].C1(C)C=CC(S(O)(=O)=O)=CC=1.O.C(=O)([O-])[O-].[Na+].[Na+]>C1C=CC=CC=1>[CH3:8][C:7]1[C:6]([CH3:10])([CH3:9])[CH2:5][CH2:4][C:3]([CH3:12])([CH3:11])[C:2]=1[CH3:13]

Participants

6

Reactant 4

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 10340Sodium CarbonateHCID 20230959HCID 20230959, compound

Product 1

HCID 131137381,2,3,3,6,6-Hexamethylcyclohex-1-eneYield 89.9%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

25.9 g of 1-hydroxy-1,2,2,5,5,6-hexamethylcyclohexane are dissolved in 600 ml of benzene and, after the addition of a spatula tip of p-toluenesulphonic acid, held at boiling temperature on a water separator for 3 hours. The mixture is cooled, treated with sodium carbonate, stirred briefly, filtered and the benzene is distilled off at normal pressure. Distillation of the residue gives 21 g of 1,2,3,3,6,6-hexamethyl-1-cyclohexene as a colourless liquid of boiling point 65°-67° C./10 mm Hg.

Workup

  1. customfor 3 hours
  2. temperatureThe mixture is cooled
  3. filtrationfiltered
  4. distillationthe benzene is distilled off at normal pressure
  5. distillationDistillation of the residue

Sources & evidence

ORD record
ord-c8fb17f11eaa43b3ad429f9a711739a3
Source dataset
uspto-grants-1986_10
Patent number
US04617146

Reaction notes

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