Synthesis and Characterization of Mono- and Di-O-Alkylated Derivatives of Methyl 3,5-Dihydroxy Benzoate

Authors

Michele Paccagnini FCRH '12, Fordham UniversityFollow
Matthew Tracey FCRH '11, Fordham UniversityFollow
J. Ryan Combs FCRH '10, Fordham UniversityFollow
Amy M. Balija, Fordham UniversityFollow

Abstract

In the course of searching for monomers for larger macromolecular structures, we attempted the bis-O-alkylation of methyl 3,5-dihydroxy benzoate (1) with (bromomethyl)cyclohexane (2). To our knowledge, no literature procedures have been published on the preparation of ethers by alkylation of a phenol substrate with (bromomethyl)cyclohexane. We were surprised to find that the mono-O-alkylated product was predominantly obtained in this reaction. This finding is in contrast with those reported for alkylations, utilizing benzyl bromide where bis-O-alkylation is the predominant reaction (Yan et al. 2011). Herein we report a convenient synthesis of the bis-alkylated product 3 in good yield.

Recommended Citation

Paccagnini, Michele FCRH '12; Tracey, Matthew FCRH '11; Combs, J. Ryan FCRH '10; and Balija, Amy M. (2014) "Synthesis and Characterization of Mono- and Di-O-Alkylated Derivatives of Methyl 3,5-Dihydroxy Benzoate," The Fordham Undergraduate Research Journal: Vol. 2: Iss. 1, Article 6.
Available at: https://research.library.fordham.edu/furj/vol2/iss1/6