Abstract
The alkylation of carboxylic acids by an ethyl moiety of boron trifluoride etherate in the absence of ethyl alcohol from the reaction system is unexpected and novel. Both aromatic and aliphatic carboxylic acids were clearly alkylated affording good yields in short reaction times with the exception of nicotinic acid that necessitated an overnight reaction. It was noted that while ortho -substituted hydroxyl groups of carboxylic acids investigated were not affected by alkylation, those of meta - and para -substituted carboxylic acids were partially etherified. Furthermore, the alkylation reaction was found to be compatible with a range of functional groups such as halogens, amino and nitro groups except for the alkene function of undecylenic acid that underwent polymerisation with concomitant alkylation of its carboxylic acid function. KEY WORDS : Carboxylic acids, Alkylation, Etherification, Functional groups, Boron trifluoride etherate Bull. Chem. Soc. Ethiop. 2018 , 32(2), 387-392. DOI: https://dx.doi.org/10.4314/bcse.v32i2.16
Highlights
The synthesis of ortho-acylphenols have aroused the interest of organic chemists not least ourselves because of their biological activities with many of the molecules present in an array of natural products [1]
We got encouraged by reports of the synthesis of ortho-acylphenols catalysed by boron trifluoride [4] and that of deoxybenzoins from respective substituted phenols and phenyl acetic acids in the presence of boron trifluoride etherate (BTE) as Lewis acid catalyst and as solvent for the acylation reactions [5]
The alkylation of carboxylic acids proceeded cleanly with good yields in the presence of boron trifluoride etherate as alkylating agent and solvent
Summary
The synthesis of ortho-acylphenols have aroused the interest of organic chemists not least ourselves because of their biological activities with many of the molecules present in an array of natural products [1]. We got encouraged by reports of the synthesis of ortho-acylphenols catalysed by boron trifluoride [4] and that of deoxybenzoins from respective substituted phenols and phenyl acetic acids in the presence of boron trifluoride etherate (BTE) as Lewis acid catalyst and as solvent for the acylation reactions [5]. In place of the anticipated acylphenols, all carboxylic acids were alkylated forming carboxylic acid ethyl esters.
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