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Canola meal, the by-product of canola oil refining, is a rich source of phenolic compounds and protein. The meal, however, is primarily utilized as animal feed but represents an invaluable source of nutraceuticals. Of particular interest are the sinapates, sinapine and sinapic acid, with the decarboxylation of the latter to form canolol. Extracting these phenolics has been carried out using a variety of different methods, although there is an urgent need for environmentally safe and sustainable methods. Microwave-assisted solvent extraction (MAE), as a green extraction method, is receiving considerable interest. Its ease of use makes MAE one of the best methods for studying multiple solvents. The formation of canolol, from sinapine and sinapic acid, is primarily dependent on temperature, which favors the decarboxylation reaction. The application of MAE, using the MultiwaveTM 500 microwave system with green extractants, was undertaken to assess its ability to enhance the yield of sinapates and canolol. This study examined the effects of different pre-treatment temperature-time combinations of 140, 150, 160, and 170 °C for 5, 10, 15, 20, and 30 min on the extraction of canolol and other canola endogenous phenolic compounds. Total phenolic content (TPC), total flavonoid content (TFC), as well as metal ion chelation (MIC) and DPPH radical activity of the different extracts were assessed. The results confirmed that extractability of canolol was optimized with methanol at 151 °C and with ethanol at 170 °C with pre-treatment times of 15.43 min and 19.31 min, respectively. Furthermore, there was a strong positive correlation between TPC and TFC (p < 0.05) and a negative correlation between TFC and DPPH radical activity. Interestingly, no significant correlation was observed between MIC and DPPH. These results confirmed the effectiveness of MAE, using the novel MultiwaveTM 500 microwave instrument, to enhance the yield of canolol. This was accompanied by substantial improvements in the antioxidant activity of the different extracts and further established the efficacy of the current MAE method for isolating important natural phenolic derivatives for utilization by the nutraceutical industry.