Isopropanol → HCID 13982253, compound

Participants

Reaction Steps

5 ml of Jones reagent (1.34 g as chromic anhydride) were added, whilst ice-cooling, to a solution of 4.30 g of dl-trans-2-hexadecyloxymethyl-3-hydroxytetrahydropyran (prepared as described in Preparation 2) in 20 ml of acetone. The mixture was then stirred at room temperature for 2 hours, after which 2 ml of isopropanol were added. The reaction mixture was then stirred for a further 10 minutes, after which it was diluted with 50 ml of ethyl acetate and then washed, in turn, with water, a saturated aqueous solution of sodium bicarbonate and a saturated aqueous solution of sodium chloride. It was then dried, and the solvent was removed by distillation. The resulting oily residue, 4.5 g, was subjected to column chromatography through 100 g of silica gel. The fraction eluted with mixtures of ethyl acetate and hexane ranging from 1:10 to 3:20 by volume gave 3.73 g of the title compound, melting at 42°-43.5° C. (hexane).

Provenance & Evidence