2,6-Dimethylcyclohexanone → 3,7-Dimethyloxepan-2-one

HRID 1529513Notes

Reaction equation

HRID 1529513 reaction equation
[CH3:1][CH:2]1[CH2:7][CH2:6][CH2:5][CH:4]([CH3:8])[C:3]1=[O:9].O.O.O.O.O.O.C(O[O-])(=O)C1C(=CC=CC=1)C([O-])=[O:20].[Mg+2].C(=O)(O)[O-].[Na+]>CO.O>[CH3:8][CH:4]1[CH2:5][CH2:6][CH2:7][CH:2]([CH3:1])[O:20][C:3]1=[O:9]

Participants

5

Reactant 3

HCID 177802,6-DimethylcyclohexanoneHCID 516892Sodium BicarbonateHCID 21894687Magnesium 2-(dioxidan-2-ide-1-carbonyl)benzoate--water (1/1/6)

Product 1

HCID 141398093,7-Dimethyloxepan-2-oneYield 47.5%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

A 250 mL round bottom flask was charged with 2,6-dimethylcyclohexanone (2.162 mL, 2.0 g, 15.85 mmol) and 126 mL of a 1:1 methanol/water mixture. The solution stirred as magnesium monoperoxyphthalate hexahydrate (MMPP, 15.68 g, 31.7 mmol) and sodium bicarbonate (2.66 g, 31.7 mmol) were added. The reaction proceeded overnight at room temperature with stirring. The following day the crude product was extracted into ethyl acetate, washed sequentially with saturated sodium bicarbonate, brine and dried over anhydrous sodium sulfate before concentrating in vacuo to give 1.07 g (47.5% yield) of 3,7-dimethyloxepan-2-one (61) as a clear, colorless oil.

Workup

  1. additionwere added
  2. extractionThe following day the crude product was extracted into ethyl acetate
  3. washwashed sequentially with saturated sodium bicarbonate, brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationbefore concentrating in vacuo

Sources & evidence

ORD record
ord-7997d3e5dced430db57d44da8c2c6c54
Source dataset
uspto-grants-2015_07
Patent number
US09090629B2

Reaction notes

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