University of Massachusetts Amherst ScholarWorks@UMass Amherst Masters Theses 1911 - February 2014 1933 A study of the intermediate steps in the preparation of alkylphenylbarbituric acids James Edward Doyle University of Massachusetts Amherst Follow this and additional works at: https://scholarworks.umass.edu/theses Doyle, James Edward, "A study of the intermediate steps in the preparation of alkylphenylbarbituric acids" (1933). Masters Theses 1911 - February 2014. 1468. Retrieved from https://scholarworks.umass.edu/theses/1468 This thesis is brought to you for free and open access by ScholarWorks@UMass Amherst. It has been accepted for inclusion in Masters Theses 1911 - February 2014 by an authorized administrator of ScholarWorks@UMass Amherst. For more information, please contact
[email protected]. A STUDY OF THE INTERMEDIATE STEPS IN THE PREPARATION OF ALKYLPHENYLBARBITURIC ACIDS JAMES EDWARD DOYLE Thesis submitted for the degree of Master of Science MASSACHUSETTS STATE COLLEGE June 1933 TABLE OF CONTENTS Page I. INTRODUCTION 1 II. THEORY AND REVIEW OF LITERATURE 2 A. Abstracts of Patents 2 B. Previous Work on Luminal 5 C. Reactions 9 D. Previous Work on Cyanophenylacetic Acid ll*. E f Previous Work on 5»5-Isopropylphenyl- barbituric Acid 17 III. EXPERIMENTAL WORK 19 A. Preparation of Luminal 19 1. Benzyl Cyanide 21 2. Ethyl Cyanophenylacetate 22 3. Ethyl Cyanoethylphenylacetate 2l\. 5,5-Sthylphenyl-^-iminobarbituric Acid25 5. 5,5-Ethylphenylbarbituric Acid 27 B. Preparation of Ethyl oc ,-f-Dicyano-oc ,f« diphenylacetoacetate 27 1. Ethyl oc ,-Y-Dicyano-cc ,v -diphenyl- acetoacetate 29 2. Ethyl y-Cyano-oc ,Y -diphenylacetoacetate 3 2 C. Preparation of Cyanophenylacetic Acid 3k 1.