Water → HCID 57184026, compound

HRID 1873093Notes

Reaction equation

HRID 1873093 reaction equation
[CH3:1][C:2]1([CH3:11])[C:7](=[CH2:8])[CH:6]([CH3:9])[CH2:5][C@@H:4]([OH:10])[CH2:3]1.C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1(C)C=CC=CC=1>[CH3:9][C:6]1[CH2:5][C@H:4]([OH:10])[CH2:3][C:2]([CH3:11])([CH3:1])[C:7]=1[CH3:8]

Participants

5

Reactant 3

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 54282312HCID 54282312, compound

Product 1

HCID 57184026HCID 57184026, compoundYield 92.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

4 g of (1R)-3,3,5-trimethyl-4-methylene-1-cyclohexanol obtained in Example 2A were dissolved in 50 ml of toluene, about 6 mg of p-toluenesulfonic acid were added and the mixture was refluxed for 45 min. It was then poured into 50 ml of water and extracted twice with 50 ml of ether. The organic phase was separated off, washed with 50 ml of saturated NaHCO3 solution, dried over MgSO4 and freed of solvent under reduced pressure. The residue was chromatographed on 150 g of silica gel with hexane/EA (4:1) to result in 3.7 g of the abovementioned product in the form of pale yellow crystals with a purity of 97% according to GC.

Workup

  1. temperaturethe mixture was refluxed for 45 min
  2. extractionextracted twice with 50 ml of ether
  3. customThe organic phase was separated off
  4. washwashed with 50 ml of saturated NaHCO3 solution
  5. dry with materialdried over MgSO4
  6. customThe residue was chromatographed on 150 g of silica gel with hexane/EA (4:1)

Sources & evidence

ORD record
ord-1fbd0de7bbae411299ef4245c0d14a52
Source dataset
uspto-grants-2000_08
Patent number
US06111125

Reaction notes

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