m-Chloroperbenzoic acid → 6-[(6,7-Epoxy-3,7-dimethyl-2-octenyl)-oxy]-2,3-dihydrobenzofuran

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Reaction Steps

18 g. of 6-[(3,7-dimethyl-2,6-octadienyl)-oxy]-2,3-dihydrobenzofuran are dissolved in 180 ml. of methylene chloride and, with stirring and ice cooling at 0°-5° C., 14.3 g. of 80% m-chloroperbenzoic acid are added portionwise. The mixture is then stirred for a further 2 hours with ice cooling. The mixture is subsequently diluted with 360 ml. of diethyl ether and washed successively with ice-cold 1-N aqueous sodium hydroxide and water. The organic phase is dried over sodium sulfate and evaporated. By chromatography on silica gel with hexane/diethyl ether (7:3 parts by volume) there is obtained pure 6-[(6,7-epoxy-3,7-dimethyl-2-octenyl)-oxy]-2,3-dihydrobenzofuran of boiling point ca. 150° C./0.001 mmHg; nD20 = 1.5346.

Provenance & Evidence