3-Phenylprop-2-Enal → N-(3-Phenyl-2-propenylidene)aniline

Participants

Reaction Steps

10 mmol aniline was dissolved in approximately 2.5 mL 80% ethyl L-lactate in water (v/v). Separately, 10 mmol of cinnamaldehyde was dissolved in approximately 2.5 mL 80% ethyl L-lactate in water (v/v). The two solutions were combined and the resulting reaction mixture was swirled until homogeneous and then allowed to sit undisturbed at room temperature for four minutes, when crystal formation was complete. Crystals were chilled, rinsed with cold brine and vacuum filtered, washed with cold water, and allowed to air dry. Some of the hydroxyl-containing imines had to be desiccated to completely remove water, especially when humidity was high. All melting points and spectroscopic data were acquired on the crude imines. However, these imines can be recrystallized from ethyl lactate or low molecular weight alcohols.

Provenance & Evidence