Phase Transfer Catalysis with Quaternary Ammonium Type Gemini Surfactants: <Emphasis Type="Italic">O</Emphasis>-Alkylation of Isovanillin

In this paper, O-alkylation of isovanillin with unusual phase transfer catalysts alkandiyl-α,ω-bis(dimethylalkylammonium bromide) dimeric surfactants (also known as gemini surfactants) is described. Some dimeric surfactants with simple hydrophobic alkyl chains and others with hydrophobic alkyl chains containing ester functionalities with different lengths were synthesized and characterized in our laboratory. The alkylation of isovanillin with alkyl halide was successively carried out in the presence of potassium carbonate and a phase transfer catalyst in tetrahydrofuran. The same reactions were also performed with both the traditional phase transfer catalyst tetrabutylammonium bromide and without any catalyst. The results were compared with those of dimeric surfactants. Consequently, it was expressed that alkandiyl-α,ω-bis(dimethylalkylammonium bromide) dimeric surfactants successively exhibit the character of phase transfer catalysts through environmentally friendly procedures under mild conditions. The most significant feature of this work is that dimeric surfactants have been determined to act as phase transfer agents.