m-Chloroperbenzoic acid → 3-Methoxy-1a,2,7,7a-tetrahydronaphtho[2,3-b]oxirene

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Reaction Steps

3.00 g (0.019M) of 1,4-dihydro-5-methoxynaphthalene are dissolved in 52 ml of methylene chloride, and cooled with an ice bath to 0°. 3.07 g (0.018M) of m-chloro-perbenzoic acid are subsequently added to this solution over the course of one minute. The ice bath is removed, and the reaction mixture is stirred for 15 hours at room temperature. The suspension is then added to a mixture of 20 ml of 10% sodium hydroxide and 40 g of ice. The organic phase is separated, and the aqueous phase is extracted twice, each time with 20 ml of methylene chloride. The combined organic phases are washed with water and sodium chloride solution, dried and concentrated by evaporation. 1a,2,7,7a-tetrahydro-3-methoxynaphth[2,3-b]oxirane is obtained (melting point 49.5°-50.5°, after purification by column chromatography, silica gel 0.063-0.200 mm, methylene chloride and recrystallisation from hexane).

Provenance & Evidence