Issue 6, 2014
From the journal:

Green Chemistry

Amidation of phenol derivatives: a direct synthesis of paracetamol (acetaminophen) from hydroquinone†

Roxan Joncour,a   Nicolas Duguet,a   Estelle Métay,a   Amadéo Ferreirab  and  Marc Lemaire*a  

* Corresponding authors

a Laboratoire de CAtalyse SYnthèse et ENvironnement (CASYEN), Institut de Chimie et Biochimie Moléculaires et Supramoléculaires (ICBMS), CNRS, UMR-5246, Université Claude Bernard Lyon 1, 43 boulevard du 11 novembre 1918, Bât. Curien/CPE, Villeurbanne, France
E-mail: marc.lemaire.chimie@univ-lyon1.fr
Fax: +33-472-43-14-08
Tel: +33-472-43-14-07

b Minakem SAS, 145 chemin des Lilas, 59310 Beuvry-la-Forêt, France

Abstract

A direct synthesis of paracetamol (acetaminophen) from hydroquinone has been developed using ammonium acetate as an amidating agent. The reaction proceeds in acetic acid at elevated temperatures without any metallic catalyst. Under these conditions, paracetamol was obtained with high yield and selectivity (>95%). The reaction has also been carried out on the multi-gram scale (44 g of hydroquinone) and a potential process has been proposed based on the recycling of the solvent and by-products. This amidation protocol has also been extended to other phenol derivatives.

Graphical abstract: Amidation of phenol derivatives: a direct synthesis of paracetamol (acetaminophen) from hydroquinone

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Article information

DOI
https://doi.org/10.1039/C4GC00166D
Article type
Communication
Submitted
30 Jan 2014
Accepted
27 Mar 2014
First published
22 Apr 2014

Green Chem., 2014,16, 2997-3002

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Amidation of phenol derivatives: a direct synthesis of paracetamol (acetaminophen) from hydroquinone

R. Joncour, N. Duguet, E. Métay, A. Ferreira and M. Lemaire, Green Chem., 2014, 16, 2997 DOI: 10.1039/C4GC00166D

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