Ethanol → 5,6-Dihydroxyhexahydro-4,7-methano-2-benzofuran-1(3H)-one

Participants

Reaction Conditions

Reaction Steps

Initially, 21.7 g (120 mmol) of 4-oxatricyclo[5.2.1.02, 6]dec-8-en-3-one [Compound (A)] was placed in a 1-L reactor equipped with a stirrer, a thermometer, a cooling tube, and a dropping funnel, was dissolved in 318 g of ethanol and was cooled to −40° C. in a Dewar bath. Separately, 19.0 g (120 mmol) of potassium permanganate (KMnO4) and 14.4 g (120 mmol) of magnesium sulfate (MgSO4) were dissolved in water heated at 60° C., and the resulting solution was added dropwise into the reactor. After the completion of the addition, the reactor was taken out from the Dewar bath, the mixture was left stand to room temperature and was aged over night. After the completion of the reaction, the reaction mixture was filtrated, the filtrate was concentrated, the concentrate was filtrated again to remove insoluble matters, and the filtrate was extracted with ethyl acetate (n=5, s/f=2/1). The ethyl acetate layer was concentrated, the deposited solid matter was washed with toluene, was filtrated, was dried and thereby yielded the title compound [Compound (E)] in a yield of 41%.

Provenance & Evidence