Methyl decanoate (MeDC) is a fatty acid methyl ester (FAME) and is an important chemical compound with global production of 31 million tons per year. However, synthesis of methyl decanoate (MeDC) via esterification of decanoic acid (DeC) with methanol by reactive distillation is operationally challenging due to the difficulty of keeping the reactants together in the reaction zone; methanol being the lightest component in the mixture can separate itself easily from the other reactant deteriorating significantly the conversion of DeC using either a conventional batch or continuous distillation column. This is probably the main reason for not applying the conventional route to MeDC synthesis. Whether a semibatch distillation column (SBD) and the recently developed integrated, conventional batch distillation column (i-CBD) offer the possibility of revisiting such chemical reactions for the synthesis of MeDC is the focus of this paper. The minimum energy consumption (Q(tot)) as the performance measure is used to evaluate the performances of each of these reactive column configurations for different ranges of methyl decanoate purity and the amount of product. It is observed that the use of i-CBD column provides much better performance than the SBD column in terms of the production time and the maximum energy savings when excess methanol is used in the feed. However, the SBD column is found to perform better than the i-CBD column when both reactants in the feed are in equal amounts. Also, the optimization results for a given separation task show that the performance of a two-reflux-interval strategy is superior to the single-reflux interval in terms of operating batch time, and energy usage rate in the SBD process at equimolar ratio.