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A Study Of The Esterification Of 2,2,4,4-Tetramethyl-1,3-Cyclobutanediol, Lewis Metzler Naylor

Dissertations and Theses @ UNI

The purpose of this research was to prepare, identify, and characterize 2,2,4,4-tetramethyl-1,.3-cyclobutanediol bischloroacetate using 2,2,4,4-tetramethyl-1,3-cyclobutanediol and monochloroacetic acid as starting materials. The synthesis of this diester has not been reported previously.

Catalyzed and uncatalyzed reactions were attempted, with the uncatalyzed having, in general, the better yield. The diester, trans-2,2,4,4-tetrametbyl-1,3-cyclobutanediol bischloroacetate (mp, 103.5-104; n²², 1.516-1.520), was isolated from a mixture of the isomers. The trans configuration of the diester was confirmed by comparing known nuclear magnetic resonance spectra to that of the diester. Infrared spectroscopy was used to confirm functional groups. Standard analytical techniques were used to determine chloride …