Pinacolone → 8-Methoxy-2,2-dimethyloctan-3,5-dione

HRID 2200825Notes

Reaction equation

HRID 2200825 reaction equation
[H-].[Na+].C[O:4][CH2:5][CH2:6][CH2:7][C:8]([O:10][CH3:11])=O.[C:12]([C:16]([CH3:18])=[O:17])([CH3:15])([CH3:14])[CH3:13]>COCCOC>[CH3:11][O:10][CH2:8][CH2:7][CH2:6][C:5](=[O:4])[CH2:18][C:16](=[O:17])[C:12]([CH3:15])([CH3:14])[CH3:13]

Participants

5

Reactant 3

HCID 6416PinacoloneHCID 24758Sodium hydrideHCID 542317Methyl 4-methoxybutanoate

Product 1

HCID 129919568-Methoxy-2,2-dimethyloctan-3,5-dioneYield 14%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

1.8 mol of sodium hydride was added to the solvent ethylene glycol dimethyl ether, and 1 mol of methyl 4-methoxybutanoate was added thereto and stirred at room temperature for 10 minutes. Then, 1.2 mol of t-butylmethylketone was added to the solution which was then stirred at 92° C. for 19 hours. Then, the solution was cooled to room temperature and quenched in 36% hydrochloric acid, after which water and dimethylether were added to and mixed with the solution, and water was removed therefrom. The resulting organic material was washed with 1 wt % sodium hydroxide and then with saturated saline and concentrated, and the residue was fractionated, thereby obtaining the intermediate 8-methoxy-2,2-dimethyloctan-3,5-dione at a yield of 14%.

Workup

  1. additionwas added
  2. stirringwas then stirred at 92° C. for 19 hours
  3. temperatureThen, the solution was cooled to room temperature
  4. customquenched in 36% hydrochloric acid
  5. additionafter which water and dimethylether were added to and
  6. additionmixed with the solution, and water
  7. customwas removed
  8. washThe resulting organic material was washed with 1 wt % sodium hydroxide
  9. concentrationwith saturated saline and concentrated

Sources & evidence

ORD record
ord-8a4bae9cbb284070b40cc4e87a517d92
Source dataset
uspto-grants-2016_06
Patent number
US09359383B2

Reaction notes

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