Acetals are germinal diether derivatives of aldehydes formed by the reaction of an aldehyde with two alcohols. Collard et al. have shown that by utilizing temperature control, benzaldehyde and pentaerythritol, when mixed in water with catalytic acid, can selectively form monoacetal derivatives. The goal of our project is to expand the substrate scope of this monoacetal selective reaction to synthesize new monoacetals and to define their structure using 2D NMR techniques. Acetals similar to our target monoacetal products are used in a variety of synthetic applications. They have served as alcohol protecting groups in route to polymer-based adhesives and synthetic glycodendrimers for nanomedicine applications in drug delivery and vaccines. Our work should help to broaden the synthetic utility of this user-friendly and environmentally benign reaction. It is also hoped that this work will produce starting material for multistep synthesis routes optimized for use in advanced-level undergraduate teaching laboratories. Preliminary results based on studies using the NMR internal standard dimethyl sulfoxide indicate that many substituted benzaldehydes will provide a level of selective monoacetal formation.

Expanding the green scope of pentaerythritol acetal formation

255th National Meeting (2018)

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