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-6b808f4fc4b3454187c25c1d078c4053

Source dataset

uspto-grants-2008_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07402608B2