Ethanol → 4-Hydroxybenzaldehyde

Participants

Reaction Conditions

Reaction Steps

The synthesized emeraldine base oligomer in an amount of 0.2 g was slowly sprinkled over a 250 ml beaker containing 150 ml tetrahydrofuran in a BRANSON ultrasonic bath. The polyaniline solution was then transferred to a 500 ml flask with flux condenser and thermometer adaptor and heated with stirring to 60° C. in a heating bath. A separate solution of 1 g (0.0082 mol) p-hydroxybenzaldehyde in 50 ml absolute ethanol was prepared and slowly added via a dropping funnel to the polyaniline solution. The reaction was allowed to proceed for at least 3 days and then transferring the reaction mixture to a rotovap flask and stripping the solvent. The greenish blue powder was thoroughly ether washed and soxhlet extracted for at least 3 days with ether. The fully washed product was vacuum dried in an oven at 60° C. and characterized by NMR, Infrared, Ultraviolet, TGA, DSC,GPC, EA and x-ray spectroscopy. Reduction with sodium borohydride and lithium hydride was achieved by reflux with the endcapped polymer in dimethylformamide, cooling the mixture, pouring ethanol and then filtering, air drying, recrystallizing in methanol and characterizing the reduced base.

Provenance & Evidence