Initially, we conducted our experiments using styrene oxide. Using the protocol set out by Green in a 1987 patent, 6 six equivalents of methanol or ethanol (with no added solvent) and 0.1% of Al(OTf) 3 were added to styrene oxide and the mixture was heated under reflux for one hour. The reaction afforded excellent yields of the glycol ether where the nucleophile had attacked at the more hindered carbon atom of the epoxide ring (Scheme 1).
