iso-Isopulegol → 1-(2-Hydroxy-4-methylcyclohexyl)ethanone, (1R,2S,4R)-

To the (1S,2R,5R)-2-Isopropenyl-5-methyl-cyclohexanol (2.07 g, 13.42 mmol) in DCM (67 mL) and MeOH (1.6 mL) at −78° C. was bubbled ozone/oxygen gas until the reaction mixture was turned blue and the excess ozone was flushed off with oxygen, Dimethyl sulfide (4.9 mL) was added at the same temperature, slowly warmed up to room temperature, stirred for over night, concentrated, purified on column chromatography using 10-20% EtOAc/hexane to give (1R,2S,4R)-1-(2-Hydroxy-4-methyl-cyclohexyl)-ethanone (1.40 g, 67%) as an oil. NMR 1H (CDCl3, 400 MHz): 4.29-4.27 ppm (m, 1H); 2.40-2.35 ppm (m, 1H); 2.19 ppm (s, 3H); 1.91-1.73 ppm (m, 5H); 1.05-0.91 ppm (m, 2H); 0.88 ppm (d, 3H).

1. customthe excess ozone was flushed off with oxygen, Dimethyl sulfide (4.9 mL)
2. additionwas added at the same temperature
3. concentrationconcentrated
4. custompurified on column chromatography

ORD record

ord-a9e9e8ed0c9f4d5a92667e4b0744d7d3

Source dataset

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08829030B2