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Prominently, it is the final intermediate in the industrial synthesis of paracetamol. Treating 4-aminophenol with acetic anhydride gives paracetamol: [8] [9] [10] It is a precursor to amodiaquine, mesalazine, AM404, parapropamol, B-86810 & B-87836 (c.f. WO 2001042204 ). 4-Aminophenol converts readily to the diazonium salt. [11]
Paracetamol, [a] or acetaminophen, [b] is a non-opioid analgesic and antipyretic agent used to treat fever and mild to moderate pain. [13] [14] [15] It is a widely available over-the-counter drug sold under various brand names, including Tylenol and Panadol. Paracetamol relieves pain in both acute mild migraine and episodic tension headache.
An industrial synthesis of paracetamol developed by Hoechst–Celanese involves the conversion of a methyl ketone to an acetanilide via a Beckmann rearrangement. [15] The thermal rearrangement that occurs in the synthesis of ketamine was claimed to be a Beckmann rearrangement according to: url.
Each precursor material is examined using the same method. This procedure is repeated until simple or commercially available structures are reached. These simpler/commercially available compounds can be used to form a synthesis of the target molecule. Retrosynthetic analysis was used as early as 1917 in Robinson's Tropinone total synthesis. [1]
Morse's cited article describes the synthesis of paracetamol from 4-aminophenol and acetic acid. [6] Phenacetin may be synthesized as an example of the Williamson ether synthesis: ethyl iodide, paracetamol, and anhydrous potassium carbonate are heated in 2-butanone to give the crude product, which is recrystallized from water. [7]
Adapted from Ellis, Frank (2002) Paracetamol: a curriculum resource, Cambridge: Royal Society of Chemistry ISBN: 0-85404-375-6. Author: WhiteTimberwolf, PNG version: Rifleman 82: Permission (Reusing this file)
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English: The direct, one-pot synthesis of paracetamol from hydroquinone and ammonium acetate as described in Green Chem., 2014,16, 2997-3002. Date: 31 January 2021: