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.
Paccagnini, Michele FCRH '12; Tracey, Matthew FCRH '11; Combs, J. Ryan FCRH '10; and Balija, Amy M.
"Synthesis and Characterization of Mono- and Di-O-Alkylated Derivatives of Methyl 3,5-Dihydroxy Benzoate,"
Fordham Undergraduate Research Journal: Vol. 2
, Article 6.
Available at: http://fordham.bepress.com/furj/vol2/iss1/6