Hydrogen Peroxide → (+/-)-{3-[2,4-Bis(methoxymethoxy)phenyl]cyclohexyl}methanol

9-Borabicyclononane (2.7 ml of a 0.5M solution in tetrahydrofuran) was added to a stirred solution of (±)-2,4-bis(methoxymethoxy)-1-(3-methylenecyclohexyl)benzene (80 mg) in tetrahydrofuran (2 ml) at 0° C. under argon. After 1 hr at 0° C., the reaction mixture was allowed to warm to ambient temperature and stirring continued. After 2 hr, the reaction mixture was cooled to 0° C. and water (0.1 ml) was added. After the effervescence had subsided, hydrogen peroxide (1 ml of a 30% w/v solution) and sodium hydroxide (1 ml of a 2M solution) were added and the mixture was allowed to warm to ambient temperature. After a further 16 hr, the reaction mixture was cooled to 0° C. Saturated aqueous sodium metabisulfite was added until no oxidant could be detected by starch iodide paper, and the reaction mixture was extracted with ethyl acetate (3×30 ml). The combined organic extracts were washed with water (20 ml), dried over magnesium sulfate, and evaporated in vacuo. The crude residue was purified by flash column chromatography (SiO2, ethyl acetate/petrol, 1:1 v/v) to furnish the title compound as a pale brown oil (46 mg, 54%); m/z (ES+) 311 (M+H)+.

1. waitAfter 2 hr
2. temperaturethe reaction mixture was cooled to 0° C.
3. temperatureto warm to ambient temperature
4. waitAfter a further 16 hr
5. temperaturethe reaction mixture was cooled to 0° C
6. extractionthe reaction mixture was extracted with ethyl acetate (3×30 ml)
7. washThe combined organic extracts were washed with water (20 ml)
8. dry with materialdried over magnesium sulfate
9. customevaporated in vacuo
10. customThe crude residue was purified by flash column chromatography (SiO2, ethyl acetate/petrol, 1:1 v/v)

ORD record

ord-0d3b6c5c7a1c4b2caee38ed5e5a16686

Source dataset

uspto-grants-2004_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06828460B2