Date of Award
1967
Document Type
Senior Scholars Paper (Open Access)
Department
Colby College. Chemistry Dept.
Advisor(s)
Reid, Evans B.
Abstract
A Historical Introduction is given as background material to the problem of the existance of an ?-hydroxy-?-substituted tetronic acid as the intermediate in the oxidation of tetronic acids to ?-diketones. Three schemes are proposed by which this intermediate may be synthesized, starting with ethyl acetoacetate. In the first scheme the ?-substituted tetronic acid is oxidized by lead tetraacetate to the ?-acetoxy-?-substituted compound. In the second and third schemes, the lead tetraacetate oxidation can be applied to the ?-substituted acetoacetic ester, or the ?-substituted acetoacetic ester can be chlorinated with sulfuric chloride and then converted to the ?-acetoxy ester. Experimental work dealing with the lead tetraacetate oxidation is described, and the difficulties encountered discussed. The yields of ethyl ?-acetoxy-?-methylacetoacetate were low and thus more work is necessary before the proposed synthetic procedures are tested further.
Keywords
Organic compounds -- Synthesis, Lactones
Recommended Citation
Hoar, Phyllis Elaine, "Synthesis of Hydroxy Tetronic Acid" (1967). Senior Scholar Papers. Paper 119.https://digitalcommons.colby.edu/seniorscholars/119
Copyright
Colby College theses are protected by copyright. They may be viewed or downloaded from this site for the purposes of research and scholarship. Reproduction or distribution for commercial purposes is prohibited without written permission of the author.