m-Chloroperbenzoic acid → 3,5-Bis-benzyloxy-4-(2-methyl-oxiranylmethyl)-benzoic acid tert-butyl ester

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Reaction Steps

To a solution of 3,5-bis-benzyloxy-4-(2-methyl-allyl)-benzoic acid tert-butyl ester (227a) (80 g, 0.18 mmol) in CH2Cl2 (500 mL) was added m-CPBA (62 g, 0.36 mol) portion-wise. The mixture was refluxed overnight. The solid was filtered and washed with CH2Cl2. The filtrate was washed with saturated aqueous Na2S2O4 (250 mL) and brine (250 mL). The organic layer was separated, dried over Na2SO4 and concentrated to give a brown oil. The crude oil was quickly purified by column chromatography (EtOAc/petroleum ether=1/10) to give the title compound (40 g, 48.2% yield) as a white solid.

Provenance & Evidence