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Paracetamol inhibits prostaglandin synthesis by reducing the active form of COX-1 and COX-2 enzymes. This occurs only when the concentration of arachidonic acid and peroxides is low. Under these conditions, COX-2 is the predominant form of cyclooxygenase, which explains the apparent COX-2 selectivity of paracetamol.
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]
4-Nitrophenol is an intermediate in the synthesis of paracetamol. It is reduced to 4-aminophenol, then acetylated with acetic anhydride. [6] 4-Nitrophenol is used as the precursor for the preparation of phenetidine and acetophenetidine, indicators, and raw materials for fungicides. Bioaccumulation of this compound rarely occurs.
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)
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.
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:
English: Beckmann Rearrangement: Celanese synthesis of paracetamol. Conversion of cyclohexanone to carpolactam involving Beckmann Rearrangement. Date: 28 March 2016:
Harmon Northrop Morse (October 15, 1848 – September 8, 1920) was an American chemist. Today he is known as the first to have synthesized paracetamol, [1] but this substance only became widely used as a drug decades after Morse's death.