Mannich Reactions using Triacetic Acid Lactone

Kent Muyskens, Kevin Basemann, George A. Kraus, Department of Chemistry, Iowa State University

ABSTRACT

BACKGROUND

Several different Mannich reactions were done using triacetic acid

lactione (TAL) as one of the components. Three different amines and
three different benzaldehydes were used creating nine possible different
products. Various solvents were used along with acetic acid as a
catalyst. Several products were created that have no listing in chemical
literature so it is likely these are the first synthesis of these compounds.

Triacetic acid lactone is demonstrated to be a versatile

biorenewable molecule with potential as a platform chemical
for the production of commercially valuable bifunctional
chemical intermediates and end products.1

RESEARCH QUESTION/HYPOTHESIS
Can new substances be created using TAL in various
Mannich reactions?

RESULTS & GRAPHICS

Structures, NMR results. TLC tests and pictures of two of the new products synthesized are shown below.

Product of one of the Mannich reactions

Structure and NMR results of two of the compounds made

Performing TLC test on sample

Doing NMR tests on the product

DISCUSSION
Nine Mannich reactions were completed using combinations of TAL, piperidine, pyrrolidine, diethylamine,
benzaldehyde, 4-nitrobenzaldehyde and 2-bromobenzaldehyde. Nine products were created and all were
tested using nuclear magnetic resonance (NMR). Each of the nine expected products was produced. Of the
nine products produced seven had no information about them in scientific literature, leading to the conclusion
that these products had not been previously synthesized.
ACKNOWLEDGEMENT
I would like to thank the National Science Foundation (NSF) and the Center for Biorenewable
Chemicals (CBiRC) for funding this research experience along with Dr. George Kraus for letting
me work in his lab and Kevin Basemann for all the help he provided me during this project.

The material presented here is based upon work supported by the National Science Foundation under Award No. EEC-0813570 and EEC-1406296. Any opinions, findings,
and conclusions or recommendations expressed in this material are those of the author(s) and do not necessarily reflect the views of the National Science Foundation.