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A Straightforward Selective Acylation of Phenols over ZSM-5 towards Making Paracetamol Precursors

1Organic Chemistry Research Division, Faculty of Mathematics and Natural Sciences, Bandung Institute of Technology, Jalan Ganesha 10, Bandung 40132, Indonesia

2Inorganic and Physical Chemistry Research Division, Faculty of Mathematics and Natural Sciences, Bandung Institute of Technology, Jalan Ganesha 10, Bandung 40132, Indonesia

Received: 29 Jun 2018; Revised: 1 Aug 2018; Accepted: 5 Aug 2018; Published: 4 Dec 2018; Available online: 14 Nov 2018.
Open Access Copyright (c) 2018 by Authors, Published by BCREC Group under

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Commercially available ZSM-5 was minimally treated as the catalyst to selectively acylate phenols. The ZSM-5 was simply immersed in ammonium nitrate in order to fill the pores with Brönsted acid to concentrate the catalytic reactions inside the pores. The reactions were carried out in liquid phase at 383 K. Acetic acid and propionic acid were chosen as the acyl substrate. Gas chromatography reveals two products which are phenyl acetate and almost exclusively para-hydroxyacetophenone meaning no ortho product observed. This para selectivity can be attributed to the pores of ZSM-5 where the reaction is assumed to be happening via intermolecular reaction. It is a relatively straightforward method in making para-hydroxyacetophenone which is known as paracetamol precursor. 

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Keywords: Acylation of Phenol; ZSM-5; Regioselectivity; Para-hydroxhyacetophenone
Funding: Riset Peningkatan Kapasitas ITB program

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Last update: 2021-07-25 09:08:27

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