Water → 2-(4-(4-Hydroxycyclohexyl)cyclohexyl)-5-n-butyl-1,3-dioxane

Participants

Reaction Conditions

Reaction Steps

In 50 ml of ethanol was dissolved 3.2 g (9.9 mmol) of the 2-(4-(4-oxocyclohexyl)cyclohexyl)-5-n-butyl-1,3-dioxane, and the solution was cooled down to 0° C. To this solution was added gradually 0.19 g (5.0 mmol) of sodium borohydride such that the liquid temperature did not exceed 15° C., and the mixture was stirred for 1 hour. Water in an amount of 50 ml was added to the reaction mixture, the product thus formed was extracted with ether, the extract was washed with 1N-hydrochloric acid and water in this turn, and the solvent was distilled off. After the residue was purified by column chromatography on silica gel (eluent: heptane/ethyl acetate=2/1), the solvent was distilled off. The residue was recrystallized from ethanol to give 1.2 g (3.7 mmol) of 2-(4-(4-hydroxy-cyclohexyl)cyclohexyl)-5-n-butyl-1,3-dioxane. Yield of this compound based on 2-(4-(4-oxocyclohexyl)cyclohexyl-5-n-butyl-1,3-dioxane was 37%.

Provenance & Evidence