Hydrogen Peroxide → 1-Methyl-7-oxabicyclo[4.1.0]heptan-2-one

At room temp., 2N aqueous sodium hydroxide (7.00 mL, 14.0 mmol), followed by 30% aqueous hydrogen peroxide (11.0 mL, 112 mmol) was added to a stirred solution of commercially available 2-methylcyclohex-2-enone (2.20 g, 20.0 mmol) in methanol (250 mL), upon which the resulting red color of the solution faded within 10 min. After stirring at room temp. for 24 h, the reaction mixture was diluted with water (200 mL) and extracted with dichloromethane (3×150 mL). The combined organic extracts were washed with water (200 mL) and dried with sodium sulfate. The solvent was removed under reduced pressure, and the resulting residue purified by chromatography on silica gel [40 g; pentane-Et2O (9:1); Rf=0.29] to furnish 1-methyl-7-oxabicyclo[4.1.0]heptan-2-one (1.18 g, 47%) as a colourless liquid.

1. customAt room temp.
2. extractionextracted with dichloromethane (3×150 mL)
3. washThe combined organic extracts were washed with water (200 mL)
4. dry with materialdried with sodium sulfate
5. customThe solvent was removed under reduced pressure
6. customthe resulting residue purified by chromatography on silica gel [40 g; pentane-Et2O (9:1); Rf=0.29]

ORD record

ord-d940052f92c74222b733b93d75f75c13

Source dataset

uspto-grants-2012_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08217185B2