(1) Oxidation: Add p-methylacetophenone, water, and anhydrous zinc chloride to a reaction vessel, stir evenly, and slowly heat to 35-40℃. Divide potassium permanganate into five equal parts, adding one part every 15-20 minutes. Control the reaction temperature at 48-55℃ during the addition. After the addition is complete, control the reaction temperature at 40-45℃ and keep it warm for 1.5 hours. Then cool it down to 17-22℃, centrifuge, and dry to obtain crude 4-acetylbenzoic acid. (2) Mix the prepared crude product with anhydrous acetic acid, heat under reflux for 0.5-1.5 hours, filter while hot, centrifuge, and dry to obtain 4-acetylbenzoic acid.
4-Acetylbenzoic Acid is an intermediate used to prepare Curcumin Analogs with anti-oxidant activities. It is also used in the synthesis of quinuclidine benzamides as agonists of α7 nicotinic acetylcholine receptors.
White to light yellow crystal powder
4-Acetylbenzoic acid was used in the preparation of an ester-derivative of paclitaxel.
4-AcDissolve the acid in 5% aqueous NaOH, extract it with Et2O, and acidify the aqueous solution. Collect the precipitate, and recrystallise it from boiling H2O (100 parts) using decolorising charcoal [Pearson et al. J Org Chem 24 504 1959, Pearson et al. J Chem Soc 265 1957, Detweiler & Amstutz J Am Chem Soc 72 2882 1950, Bordwell & Cooper J Am Chem Soc 74 1058 1952]. [Beilstein 10 IV 2769.]
