Dimethyl Sulfoxide → HCID 22375156, compound

Participants

Reaction Steps

DMSO in an amount of 2.13 ml (0.03 mol) was added dropwise to a mixture of 1.74 ml (0.02 mol) of oxalic acid chloride and 40 ml of dichloromethane at -50° C. and stirred for 10 min. While keeping inside of the reaction system at -60°C., this solution was added dropwise with a solution of 2.82 g (0.01 mol) of the 4-(4-propylcyclohexyl)-(3-hydroxypropyloxy)cyclohexane obtained in the second stage and dissolved in 20 ml of dichloromethane and stirred for 1 hour. To this solution was added 14 ml of triethylamine, temperature of the solution was returned to a room temperature, stirred for 15 min, and the solution was added with 80 ml of an aqueous solution saturated with ammonium chloride. The organic layer was separated and dried over anhydrous magnesium sulfate. After the magnesium sulfate was separated, the solvent was distilled off under a reduced pressure, and the residue was subjected to a silica gel column chromatography (eluate: toluene/ethylacetate (9/1)) to obtain 1.93 g of a crude 4-(4-propylcyclohexyl)-(3-oxopropyoxy) cyclohexane. This product was recrystallized from 12 ml of ethanol to obtain 1.3 g (yield 46%) of 4-(4-propylcyclohexyl)-(3-oxopropyloxy)cyclohexane.

Provenance & Evidence