Unexpected Dimer from Demethylization Reaction of Eugenol under Acidic Conditions
| Autor: | Didin Mujahidin, Anita Alni, Meilisa Dara Puspita |
|---|---|
| Rok vydání: | 2019 |
| Předmět: |
natural products
General Mathematics Dimer General Physics and Astronomy Medicinal chemistry General Biochemistry Genetics and Molecular Biology law.invention chemistry.chemical_compound Nucleophile clove essential oil law Fourier transform infrared spectroscopy lcsh:Science lcsh:Science (General) Essential oil Demethylation dimerization Multidisciplinary Chemistry demethylation General Chemistry General Medicine Eugenol Proton NMR General Earth and Planetary Sciences Lithium chloride lcsh:Q General Agricultural and Biological Sciences eugenol lcsh:Q1-390 |
| Zdroj: | Journal of Mathematical and Fundamental Sciences, Vol 51, Iss 1, Pp 60-67 (2019) |
| ISSN: | 2338-5510 2337-5760 |
| Popis: | Eugenol is an alkenyl phenol compound obtained as an essential oil from different parts of the clove such as its leaves and flowers. The essential oil from cloves can contain up to 90% eugenol, which is mainly responsible for its aroma. Eugenol is an interesting compound due to its simplicity and richness in functionalities, making it a valuable building block in synthesis. One of the key steps in eugenol transformation is demethylation to produce a hydroxycavicol. Demethylation is commonly carried out using a nucleophilic or an acidic method. In this study, a simple yet reliable nucleophilic method for demethylation using lithium chloride (LiCl) was attempted. The product was characterized by NMR, FTIR and HRMS spectroscopy. The absence of a methoxy signal at 3.5-4 ppm in the 1 H NMR spectrum suggests that demethylation was successful. The HRMS result showed m/z 149.0596, confirming the formation of product. The demethylation reaction under acidic conditions formed a dimer of eugenol with the methoxy group still intact. This was supported by the 1 H NMR data, which showed methoxy signals at 3.85 and 3.82 ppm and integration in the aromatic region, which suggests a dimer structure. |
| Databáze: | OpenAIRE |
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