Synthesis of 4-Hydroxy-4-(4-nitrophenyl)butan-2-one using p-Nitro Benzaldehyde and Acetone in Aqueous Micellar Media using L-Proline

Abstract

Abstract When the asymmetric aldol reactions are catalyzed by amino acids in water, a certain amount of organic solvents such as ethanol, tetrahydrofuran still had to combine with water to dissolve the organic aldehydes and promote the reaction. But to protect the environment our aim is to completely eliminate the use of organic solvent, therefore we have started to investigate a new system for amino acids catalyzed aldol reaction in water without using any organic solvents. Mainly we use organic solvent to form a homogeneous phase for all reactants which is not possible if the solvent is water, as it makes most organic substances spasingly soluble in water. This drawback could be overcome if we use surfactants, which solubilise organic compounds in water. Thereafter, we planned to use cetyl trimethyl ammonium bromide (CTAB) as surfactant to solubilise the substrate p-nitrobenzaldehyde (PNB) and to perform in this aqueous micellar solution a L-proline catalyzed aldol reaction. A quite different mechanism has been proposed in water.