2014 Participants
< Back

NAME: Isaiah Dishner

PROJECT TITLE: Preparation of 2-(3,5-dichlorophenyl)-1,3-cyclopentadione

The compound N-(3,5-dichlorophenyl)succiniminde (NDPS) was first synthesized in the early 1970s as an agricultural fungicide. Subsequent animal studies have indicated that both acute and prolonged exposure to this compound induces nephrotoxicity. This has led some researchers to suggest that NDPS can be used as a model compound to study chemically induced interstitial nephritis. Toxicity studies using analogs of NDPS have aimed to demonstrate the effects that specific structural components have on NDPS toxicity. One analog that has not been studied is 2-(3,5-dichlorophenyl)-1,3-cylclopentanedione. However, there is no evidence to suggest that this compound has ever been synthesized previously. Therefore, a synthetic route must first be prepared before the toxicity of this compound can be studied.

In our research, a route for preparing 2-(3,5-dichlorophenyl)-1,3-cylclopentanedione from diethyl succinate and 3,5-dichlorobenzaldehyde has been hypothesized. This reaction proceeds through two steps. In the first step, an intramolecular acyloin condensation is performed on diethyl succinate, and the resulting product is trapped as 1,2-bis(trimethylsilyloxy)cyclobutene by reaction with trimethylsilyl chloride. A pinacol rearrangement using the intermediate compound and 3,5-dichlorobenzaldehyde yields the product. At the present time, 1,2-bis(trimethylsilyloxy)cyclobutene has been synthesized. Further experiments have revealed a number of important properties of this compound. In particular, a failed distillation has shown that 1,2-bis(trimethylsilyloxy)cyclobutene decomposes at a temperature of roughly 100˚C. The second step has not been attempted yet. Furthermore, 3,5-dichlorobenzaldehyde is too expensive to use immediately in the pinacol rearrangement without first assuring that it will react as predicted. As a result, the next step in this research will be to test second step using the cheaper 2,4-dichlorobenzaldehyde as the aldehyde.