Acetone → HCID 15405233, compound

Participants

Reaction Steps

Into a solution of acetone (116 g; 2 mol) and a 3% aqueous solution of sulfuric acid (35 g) was added 8,9-epoxy-p-menthan-3-ol (17 g; 0.1 mol), and the mixture was stirred at room temperature for 16 hours. Then, the acetone was distilled and recovered, and the concentrated solution was mixed with water (40 ml) and heated to within 80° C. of the distilling temperature to completely recover the acetone. The remaining aqueous solution was cooled, neutralized with a 10% aqueous solution of sodium carbonate, and saturated with sodium chloride. The reaction product was extracted with THF, dried over anhydrous magnesium sulfate, and concentrated to give a crude product (19 g). The crude product was purified by column chromatography on silica gel. That is, the crude product was eluted with 50% ethyl acetate-n-hexane, then eluted with ethyl acetate only, and the eluate was concentrated to give a highly pure title compound (4) (7 g; a mixture of diastereomers). This was a mixture of solid and liquid, and the mixing ratio of diastereomers was calculated as 7:3 by measuring with NMR. Analytical results on the title compound are given below. Optical rotation [α]D25=+15.6 (c=1, EtOH)

Provenance & Evidence