A Study Involving the Synthesis of Unsymmetrical Dibenzylcarbinols

Author

Edward Horning, Fort Hays Kansas State College

Document Type

Thesis - campus only access

DOI

10.58809/DJRS2579

Date of Award

Spring 1961

Degree Name

Master of Science (MS)

Department

Chemistry

Advisor

Kenneth L. Marsi

Abstract

The synthesis of some unsymmetrical dibenzylcarbinols was attempted through a Grignard reaction involving para-substituted benzyl halides and phenylacetaldehyde. It was found that the Grignard reaction does not produce the desired carbinols. Evidence is presented to show that the Grignard reagent initiates an aldol condensation of the phenylacetaldehyde which is further catalyzed by the alkoxide ions formed in the reaction. The resulting aldol undergoes a Grignard reaction to form a substituted pentanediol which partially dehydrates upon distillation at reduced pressure. A reaction mechanism is proposed to account for the formation of the reaction products. An alternate synthetic route was proposed for the preparation of unsymmetrical dibenzylcarbinols, and 1-phenyl-3-(p-chlorophenyl)-2-propanol was successfully prepared in this manner. The 3, 5-dinitrobenzoate and the phenylurethan derivatives of this carbinol were also prepared. This is the first reported synthesis for 1-phenyl-3-(p- chlorophenyl)-2-propanol.

Comments

For questions contact ScholarsRepository@fhsu.edu

Recommended Citation

Horning, Edward, "A Study Involving the Synthesis of Unsymmetrical Dibenzylcarbinols" (1961). Master's Theses. 706.
DOI: 10.58809/DJRS2579
Available at: https://scholars.fhsu.edu/theses/706

Rights

© 1961 Edward Horning