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Alkylbenzene to Acid



Example 1

To a solution of the SM (50 g, 159. 2 mmol) in pyridine (300 mL) and H2O (300 mL) was added KMnO4 (100 g, 637.2 mmol) portionwise. The reaction mixture was stirred at 85 C for 6 h. After completion, the mixture was filtered through celite and the celite pad was washed with EtOH (2 x 1.0 L). The filtrate was concentrated to half its volume, then acidified with 1.5N HCl (500 mL) to pH ~2. The resulting precipitate was collected by filtration, washed with ether (2 x 150 mL), and dried in vacuo to provide the product as a white solid which was used in the next step without further purification. [30 g, 55.0%] [WO2015051043, page 114]