Reaction #631992

Reaction equation

3-(dodecylthio)-1-(2,6,6-trimethyl-3-cyclohexen-1-yl)-1-butanone

EtOH

→

title compound

Yield 38.0%

3-(dodecylsulfinyl)-1-(2,6,6-trimethyl-3-cyclohexen-1-yl)-1-butanone

Yield 38.0%

Solvents

MeOH

H2O

Conditions

Workup

1. 1
   Otherwas brought to room temperature
2. 2
   Extractiontitle compound extracted (ether/brine)
3. 3
   WashThe organic phase was washed with aqueous NaHSO3, H2O, saturated aqueous NaHCO3
4. 4
   Dryingbrine, dried over Na2SO4
5. 5
   Concentrationconcentrated

Procedure

A solution of 3-(dodecylthio)-1-(2,6,6-trimethyl-3-cyclohexen-1-yl)-1-butanone (2.00 g; 5.10 mmol) in MeOH (20 ml) was added at 0° C. to a solution of NaIO4 (1.14 g, 5.30 mmol) in H2O (11 ml). The temperature was brought to room temperature and EtOH (30 ml) was added. The suspension was stirred for 15 h and title compound extracted (ether/brine). The organic phase was washed with aqueous NaHSO3, H2O, saturated aqueous NaHCO3, then brine, dried over Na2SO4, and concentrated. (16.2 g). Flash chromatography (cyclohexane/ethyl acetate=7:3, then 1:1) on SiO2 (40 g) afforded 803 mg of the title compound (38%).

Source