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Synthesis of 4-Hydroxy-2-Methylchalcone from meta-Cresol Formilation Product and Its Activities as an Antibacteria

Chemistry Department, Faculty of Sciences and Mathematics, Diponegoro University, Indonesia

Received: 20 Aug 2018; Revised: 22 Oct 2018; Accepted: 23 Oct 2018; Published: 31 Oct 2018.
Open Access Copyright 2018 Jurnal Kimia Sains dan Aplikasi under http://creativecommons.org/licenses/by-sa/4.0.

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Abstract

Research on the synthesis of 4-hydroxy-2-methylchalcone from 4-hidroksi-2-metilbenzaldehida as formilated meta-cresol product and its antibacterial activity test has been conducted. As the first step, synthesis of 4-hydroxy-2-methylbenzaldehyde was carried out by treatment meta-cresol with chloroform through the Reimer-Tiemann formylation. Product is a brown solid with 23.94% yields. Furthermore, the 4-hydroxy-2-methylchalcone was synthesized using the 4-hydroxy-2-methylbenzaldehyde and acetophenone through the Claisen-Schmidt reaction. The product is a brownish yellow solid with 29.74% yields. Antibacterial test against Escherichia coli and Staphylococcus aureus bacteria was carried out by comparing the activity of 4-hydroxy-2-methylchalcone with 4-hydroxy-3-methoxychalcone, and chalcone compounds. The antibacterial activity test showed that the 4-hydroxy-2-methylchalcone compound, 4-hydroxy-3-methoxychalcone, and chalcone compounds gave a better antibacterial activity against Escherichia coli than the Staphylococcus aureus.

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Keywords: Claisen-Schmidt; Chalcone; Reimer-Tiemann; Antibacterial

Article Metrics:

  1. M. Hapsari, Tri Windarti, Purbowatiningrum Ria Sarjono, Ngadiwiyana, Ismiyarto, Synthesis of 4-hydroxy-3-methylchalcone from Reimer-Tiemann reaction product and its antibacterial activity test, IOP Conference Series: Materials Science and Engineering, 349, 1, (2018) 012036 https://doi.org/10.1088/1757-899X/349/1/012036
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