Chemistry
Document Type
Oral Presentation
Location
Indianapolis, IN
Subject Area
Chemistry
Start Date
11-4-2014 9:45 AM
End Date
11-4-2014 10:45 AM
Sponsor
Stacy O'Reilly (Butler University)
Description
Glycerol is one of the byproducts in the production of biofuels and there is a growing interest in the potential of glycerol as a chemical feedstock. Glycerol can undergo preferential 1,2 cyclic acetalformation with benzophenone under solvent free conditions in the presence of catalytic In(OTf)3 and stoichiometric orthoformate to form a racemic 2,2 substituted dioxolane. Conversion of the unreacted primary alcohol to an ester can be accomplished through reaction with a resolved chiral carboxylic acidor acid chloride. Resolution of the esters yields diastereomerically pure material in two steps from the glycerol starting material.
Synthesis and Resolution of a Substituted Dioxolane from Glycerol
Indianapolis, IN
Glycerol is one of the byproducts in the production of biofuels and there is a growing interest in the potential of glycerol as a chemical feedstock. Glycerol can undergo preferential 1,2 cyclic acetalformation with benzophenone under solvent free conditions in the presence of catalytic In(OTf)3 and stoichiometric orthoformate to form a racemic 2,2 substituted dioxolane. Conversion of the unreacted primary alcohol to an ester can be accomplished through reaction with a resolved chiral carboxylic acidor acid chloride. Resolution of the esters yields diastereomerically pure material in two steps from the glycerol starting material.