Organic synthesis with sulphones. Part 14. Nucleophilic substitution on styryl sulphones; a new route to arylacetaldehydes

Abstract

Condensation of sulphones with aromatic aldehydes in an alkaline medium readily gives β-hydroxy-sulphones which can be dehydrated to β-styrylsulphones. When these are treated with one molar equivalent of sodium alkoxides in dimethyl sulphoxide at room temperature, β-alkoxystyrenes are formed by ready nucleophilic substitution. Treatment of the hydroxy-sulphones directly with an excess of sodium methoxide leads to the corresponding dimethyl acetals. This is a new and potentially useful way to prepare arylacetaldehyde derivatives.