Regioselective epoxide ring opening mediated by iron oxide-pillared clay

Iron oxide pillared clays (FeOx-pillared clays) such as FeOx-pillared hectorite and FeOx-pillared bentonite were synthesized by the intercalation of iron (III) chloride into clay interlayers and calcined at 300 degrees C. The synthesized catalysts were utilized for styrene oxide ring opening by methanol, comparing with raw clays and Fe2O3. FeOx-pillared bentonite efficiently catalyzed the ring-opening of epoxides to produce beta-alkoxyalcohols in excellent yields under extremely mild reaction conditions. The quantitative yield of 2-methoxy-2-phenylethanol was obtained using 30 wt% FeOx-pillared bentonite to styrene oxide at 70 degrees C for 10 min. The optimized condition was applied to the ring opening of different epoxides such as 1-dodecene oxide, cyclohexene oxide, butyl glycidyl ether, tert-butyl glycidyl ether and alpha-pinene oxide to furnish the desired products in moderate to excellent yields. (c) 2013 Elsevier B.V. All rights reserved.