5,6-Dimethoxynaphthalene-2-carboxylic acid was synthesized in 7 steps and with an overall yield of 46%.
📌 3 Key Takeaways
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Objective & Hypothesis:5,6-Dimethoxynaphthalene-2-carboxylic acid was synthesized in 7 steps and with an overall yield of 46%.
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Key Findings & Data:Bromination of 2-naphthol, and methylation with dimethyl sulfate followed by Friedel-Crafts acylation with AcCl gave 2-acetyl-5-bromo-6-methoxynaphthalene. 2-Acetyl-5-bromo-6-methoxynaphthalene was converted to 5-bromo-6- methoxynaphthalene-2-carboxylic acid by a haloform reaction.
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Conclusion & Impact:The 5-bromo-6-methoxynaphthalene-2-carboxylic acid and 5,6-dimethoxynaphthalene-2-carboxylic acid were found to have in vitro antibacterial activity against some pathogenic bacteria.
🔬Design:Research Article
📍Scope:Comprehensive Sample
⚙️Variables:Domain Parameters
Abstract
5,6-Dimethoxynaphthalene-2-carboxylic acid was synthesized in 7 steps and with an overall yield of 46%. Bromination of 2-naphthol, and methylation with dimethyl sulfate followed by Friedel-Crafts acylation with AcCl gave 2-acetyl-5-bromo-6-methoxynaphthalene. 2-Acetyl-5-bromo-6-methoxynaphthalene was converted to 5-bromo-6- methoxynaphthalene-2-carboxylic acid by a haloform reaction. The esterification of the acid with methanol, methoxylation with NaOCH3 in the presence of CuI and subsequent de-esterification with NaOH afforded 5,6-dimethoxynaphthalene-2-carboxylic acid. The 5-bromo-6-methoxynaphthalene-2-carboxylic acid and 5,6-dimethoxynaphthalene-2-carboxylic acid were found to have in vitro antibacterial activity against some pathogenic bacteria.
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Cite This Article
ÖZDEMİR, H., SEÇEN, H., UĞUZ, M. T., GÖKSU, S. (2022). A concise synthesis and the antibacterial activity of 5,6-dimethoxynaphyhalene-2-carboxylic acid. Turkish Journal of Chemistry, Cilt: 29 - Sayı: 2, 199–205. https://ajindex.com/articles/602210
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