m-Chloroperbenzoic acid → 5,7-Dimethyl-4-hydroxy-6,8-dioxabicyclo(3.2.1)octane

Participants

Reaction Steps

A solution of 11.60 g of 16B in 25 ml of methylene chloride was added drop by drop to a stirred solution of 16.44 g of m-chloroperoxybenzoic acid in 150 ml of methylene chloride under a nitrogen atmosphere at 3° C.±10° C. The mixture was allowed to warm to room temperature and after 2 hours was washed with 800 ml of 25% aqueous potassium carbonate solution and saturated aqueous sodium chloride solution, dried (MgSO4) and stripped of solvent. The residue was chromatographed (high pressure liquid) over silica gel, using in sequence one liter each of six liquids: hexane, and five mixtures of ethyl acetate and hexane, as eluents, the volume ratios of the two components in the mixtures being, respectively: 210/790; 400/600; 400/600; 560/440; 800/200. One set of fractions was collected and stripped of solvent to give 5,7-dimethyl-4-hydroxy-6,8-dioxabicyclo(3.2.1)octane (18A), as a liquid, b.p.: not determined.

Provenance & Evidence