Chalcones have traditionally been synthesized via a one-step Aldol Condensation between an acetophenone and benzaldehyde. Using cinnamaldehyde analogs as the aldehyde starting material yields chalcones with a conjugated diene. The starting materials are readily available, and this reaction can be performed solventless, making it an excellent example of green chemistry. This poster will describe analogs have been synthesized, using different substitution patterns on the benzene rings which make these Aldol compounds a useful tool for learning 1H NMR coupling patterns including shielding/de-shielding effects for an organic chemistry or spectroscopy course. The trans vinylic proton coupling from diene part of the molecule can be complex, but this can be simplified by using α-methyl cinnamaldehyde and various substituted acetophenones as starting materials. Aromatic ketones such as 1-tetralone and 1-indanone have also been used in addition to other cinnamaldehydes with substitution on the benzene ring. The reactivity of the ketones and aldehydes used will also be discussed.

Green, solventless synthesis of novel Aldol condensation products-a method to introduce green chemistry and 1D NMR spectroscopic iinterpretation

ACS Spring 2022

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.