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An improved procedure for the "one-pot" preparation of cathecols from methylenedioxy-ring cleavage reaction of safrole derivatives with aluminum chloride is described. In substrates substituted by conjugated electron-withdrawing groups (carboxyaldehyde or nitro groups) the regioselective formation of the easily isolable chloromethyl ether intermediates was observed. From these intermediates the syntheses of mono-O-methylated phenols (3-hydroxy-4- methoxybenzaldehyde, 2-bromo-4-methoxy-5-hydroxybenzaldehyde, 2-nitro-4-methoxy-5- hydroxybenzaldehyde and 2-methoxy-4-(2-oxoprop-1-yl)-5-nitrophenol) were accomplished. Based on these experimental data and semi-empirical (MNDO) molecular orbital calculations, a mechanistic rationale that explains the observed regioselectivities was also proposed.

journal of the brazilian chemical society

The reaction of safrole derivatives with aluminum chloride: improved procedures for the preparation of catechols or their mono-O-Methylated Derivatives and a mechanistic interpretation