Cyclohexanone → 1,5-Dioxaspiro(5.5)undecane

HRID 914488Notes

Reaction equation

HRID 914488 reaction equation
[C:1]1(=[O:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:8](O)[CH2:9][CH2:10][OH:11]>C1(C)C=CC=CC=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[O:7]1[C:1]2([CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)[O:11][CH2:10][CH2:9][CH2:8]1

Participants

5

Reactant 2

HCID 7967CyclohexanoneHCID 104421,3-Propanediol

Product 1

HCID 90961,5-Dioxaspiro(5.5)undecaneYield 98.1%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 1140TolueneSolvent

Procedure

Cyclohexanone (7.94 g) was dissolved in toluene (200 mL), 1,3-propanediol (12.3 g) and p-toluenesulfonic acid monohydrate (0.1 g) were added thereto, and the mixture was heated under reflux for 1.5 hr while removing water being produced. The temperature was allowed to cool to room temperature, and the mixture was washed with saturated aqueous sodium hydrogen carbonate solution and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to give the title compound (12.4 g) as a colorless oil.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 1.5 hr
  3. customwhile removing water being
  4. customproduced
  5. washthe mixture was washed with saturated aqueous sodium hydrogen carbonate solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-6593f7c6d8b141bab5a085b90fa7696d
Source dataset
uspto-grants-2011_09
Patent number
US08026370B2

Reaction notes

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