Water → 1,3,3,6,6-Pentamethylcyclohex-1-ene

HRID 542906Notes

Reaction equation

HRID 542906 reaction equation
[CH3:1][C:2]1(O)[CH2:7][C:6]([CH3:9])([CH3:8])[CH2:5][CH2:4][C:3]1([CH3:11])[CH3:10].C1(C)C=CC(S(O)(=O)=O)=CC=1.O.C(=O)([O-])[O-].[Na+].[Na+]>C1C=CC=CC=1>[CH3:1][C:2]1[C:3]([CH3:11])([CH3:10])[CH2:4][CH2:5][C:6]([CH3:9])([CH3:8])[CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 10340Sodium CarbonateHCID 230492381,2,2,5,5-Pentamethylcyclohexan-1-ol

Product 1

HCID 230492391,3,3,6,6-Pentamethylcyclohex-1-eneYield 78.2%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

22.6 g of 1,2,2,5,5-pentamethylcyclohexanol are dissolved in 280 ml of benzene and, after the addition of 100 mg of p-toluenesulphonic acid, the mixture is boiled on a water separator for 7 hours. After cooling the solution, some solid sodium carbonate is added thereto, the mixture is filtered and the filtrate is evaporated at normal pressure. The residue is distilled in a water-jet vacuum. There are obtained 15.8 g of 1,3,3,6,6-pentamethylcyclohexen as a colorless liquid, b.p. 56°-57° C./17 mm.

Workup

  1. temperatureAfter cooling the solution
  2. filtrationthe mixture is filtered
  3. customthe filtrate is evaporated at normal pressure
  4. distillationThe residue is distilled in a water-jet vacuum

Sources & evidence

ORD record
ord-e1d8e392d7434c5db9d2d793a7334c61
Source dataset
uspto-grants-1987_04
Patent number
US04659735

Reaction notes

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