Diethyl Ether → 1a,2,7,7a-Tetrahydronaphtho[2,3-b]oxiren-3-ol

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Reaction Steps

An amount of 25.0 g of m-chloroperbenzoic acid is added over 10 minutes to an ice-cooled solution of 14.6 g of 5,8-dihydro-1-naphthol (prepared as described in Org. Syn., Coll. Vol. IV. pg. 887) in 225 ml of ethyl acetate. After 16 hours at ambient temperature the slurry is poured into a cooled, stirred mixture of 300 ml each of ether and 10% sodium bicarbonate. After 15 minutes the organic phase is separated, washed with water, saturated salt solution and dried. Solvent removal gives an oil which is triturated with two 100 ml portions of boiling hexane. The residue is recrystallized from 150 ml of 1:1 hexane-ethyl acetate to give 6.6 g of 5,6,7,8-tetrahydro-6,7-epoxy-1-naphthol, melting point 143°-146° C. Two further recrystallizations of a small sample give the analytical sample melting point 149.5°-151° C.

Provenance & Evidence