Abstract
A highly efficient synthesis of alkyl ferulates under microwave irradiation is described. The time of these reactions ranged from 3 to 5 minutes, which was much shorter than the traditional synthetic methods, and the alkyl ferulates were obtained in higher yields.
Highlights
IntroductionIt is well established that under normal conditions, there is a steady state balance between prooxidants and antioxidants, which is necessary to ensure the optimal efficiency of antioxidant defenses
It is well established that under normal conditions, there is a steady state balance between prooxidants and antioxidants, which is necessary to ensure the optimal efficiency of antioxidant defenses.when the rate of free radical generation exceeds the capacity of antioxidant defenses, oxidative stress ensues, with severe damage to the cell [1]
In the classical method of esterification ferulic acid was refluxed with alcohols in the presence of various catalysts, such as concentrated sulfuric acid, hydrogen chloride, boron trifluoride, aluminum chloride, trifluoroacetic anhydride, polyphosphate ester, neodymium oxide, dicyclohexylcarbodiimide, graphite bisulfate, etc [8,9,10], but it was difficult to avoid the disadvantages of using these catalysts, such as long reaction times, low yield, expensive reagents and tedious operation
Summary
It is well established that under normal conditions, there is a steady state balance between prooxidants and antioxidants, which is necessary to ensure the optimal efficiency of antioxidant defenses. In the classical method of esterification ferulic acid was refluxed with alcohols in the presence of various catalysts, such as concentrated sulfuric acid, hydrogen chloride, boron trifluoride, aluminum chloride, trifluoroacetic anhydride, polyphosphate ester, neodymium oxide, dicyclohexylcarbodiimide, graphite bisulfate, etc [8,9,10], but it was difficult to avoid the disadvantages of using these catalysts, such as long reaction times, low yield, expensive reagents and tedious operation. In 2002, Lee’s group reported a facile and efficient method for the conversion of ferulic acid to the corresponding alkyl carboxylates with trialkyl orthoacetate under microwave irradiation under solvent-free and neutral reaction conditions [18], but their method could only be applied to trimethyl orthoacetate and triethyl orthoacetate because trialkyl orthoacetates with long lined carbon chains or branched carbon chains could not be synthesized. The aim of this study was to establish an efficient strategy of synthesizing alkyl ferulates under the microwave irradiation, and to evaluate its efficiency in comparison with the traditional method
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