tert-Butanol → 2,2,5,5,-Tetramethylcyclopentanone

HRID 986863Notes

Reaction equation

HRID 986863 reaction equation
[C:1](O)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].S([O:13][CH3:14])(OC)(=O)=O>O>[CH3:2][C:1]1([CH3:4])[CH2:3][CH2:2][C:1]([CH3:4])([CH3:3])[C:14]1=[O:13]

Participants

5

Reactant 3

HCID 6386tert-ButanolHCID 6497Dimethyl SulfateHCID 24758Sodium hydride

Product 1

HCID 1382872,2,5,5,-Tetramethylcyclopentanone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

After cooling, 100 ml of t-butanol was slowly added dropwise thereto to decompose excess sodium hydride, and then 1.0 l of water was added thereto. The reaction mixture was further heated for 2 hours under reflux to decompose excess dimethyl sulfate. After cooling, the resulting two layers were separated and the organic layer was washed with aqueous saturated sodium chloride solution, and dried over anhydrous sodium sulfate. The solvent was distilled away under reduced pressure, and the residue was distilled under reduced pressure, whereby 59 g of 2,2,5,5-tetramethylcyclopentanone was obtained (b.p. 55° C./20 mmHg).

Workup

  1. temperatureAfter cooling
  2. temperatureThe reaction mixture was further heated for 2 hours
  3. temperatureunder reflux
  4. temperatureAfter cooling
  5. customthe resulting two layers were separated
  6. washthe organic layer was washed with aqueous saturated sodium chloride solution
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationThe solvent was distilled away under reduced pressure
  9. distillationthe residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-e087fb18db9247debdd4ed957d7ca7bc
Source dataset
uspto-grants-1987_12
Patent number
US04716241

Reaction notes

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