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Synthesis of β-hydroxy ethers

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Epoxides undergo rapid ring opening with a range of alcohols in the presence of catalytic amount of carbon tetrabromide under mild and convenient conditions to afford the corresponding β-alkoxy alcohols and 1,2-diols in high yields with high regioselectivity.
J. S. Yadav, B. V. S. Reddy, K. Harikishan, Ch. Madan, A. V. Narsaiah, Synthesis, 2005, 2897-2900.


Epoxides can be cleaved in a regio- and stereoselective manner under neutral conditions with water, alcohols and acetic acid in the presence of catalytic amounts of decatungstocerate(IV) ion, affording the corresponding diols, β-alkoxy and β-acetoxy alcohols in high yields.
V. Mirkhani, S. Tangestaninejad, B. Yadollahi, L. Alipanah, Tetrahedron, 2003, 59, 8213-8218.