Publication Date


Document Type

Honors Thesis




Anesthetics, Stereoisomers, Cyclohexane-Synthesis, Cyclohexane-Purification, Cyclohexanol, Reduction


The goal of this project is to synthesize and separate individual diastereomers of 2,6-dimethylcyclohexanol and other 2,6-disubstituted cyclohexanols, molecules of interest as possible anesthetics (Figure 1). Anesthetics have been used for over 150 years, but many of the mysteries surrounding this important class of drugs remain still undiscovered. For example, propofol (sold under the name of DiprivanОВ) is one of the most common anesthetics in use today, yet its use is accompanied by risks and side effects (Figure 2). As a result, research has strived to uncover newer and safer anesthetics that would lead to greater testing and understanding of anesthetics in general. With that in mind, 2,6- dimethylcyclohexanol was synthesized, due to its structural similarity to propofol, to serve as another possible anesthetic. This work, as part of an interdepartmental collaboration, will allow the Hall group in the Neuroscience Department at Smith College to build upon their previous work testing cyclohexanol derivatives for their anesthetic potencies through in vivo and in vitro testing. This project focused on 2,6-dimethylcyclohexanol because it had one of the strongest anesthetic potencies and there is ample research on asymmetric syntheses and stereochemical properties of this particular molecule. Figure 1. The structure of 2,6-dimethylcyclohexanol. Figure 2. The structure of propofol (2,6-diisopropylphenol, sold as DiprivanОВ).




74 p. : ill. (some col.) Honors project-Smith College, 2013. Includes bibliographical references (p. 73-74)