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2-Methoxynaphthalene

Methyl 2-naphthyl ether 2-Naphthol methyl ether 2-Naphthyl methyl ether β-Methoxynaphthalene β-Methyl naphthyl ether β-Naphthol methyl ether Nerolin Yara yara

2-Methoxynaphthalene, also called β-naphthol methyl ether, nerolin, or yara yara, is a stabilizer found in gunpowder, particularly smokeless gunpowders. It is soluble in alcohol, and insoluble in water and dipropylene glycol.

Studies have also been done on the antiinflammatory effect of β-naphthol methyl ether and on how it behaves in time-resolved resonance Raman studies.

Synthesis and uses

Nerolin can be prepared by alkylation of β-naphthol with dimethyl sulfate.

Alternative syntheses rely on the reaction of 2-Naphthol with iodomethane and KOH (Williamson ether synthesis), or by the reaction with methanol in concentrated sulfuric acid solution.

It has a faint but persistent odor and used to be a scented compound found in soap and other products.

Applications

The Friedel–Crafts acylation with propionyl chloride gives 2-propionyl-6-methoxynaphthalene (Promen) [2700-47-2]. This compound has known uses in the synthesis of Doisynoestrol & Methallenestril.

Acetylation gives 2-Acetyl-6-methoxynaphthalene, which has historical use in the synthesis of Naproxen.

Nerolin had found use in the synthesis of 6-Methoxy-1-tetralone [1078-19-9], which is a critical compound for manifold reasons.

References

References

  1. (2014). "Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book)". [[Royal Society of Chemistry.
  2. [http://www.thegoodscentscompany.com/data/rw1012111.html "2-methoxynaphthalene"], ''The Good Scents Company'', 2012
  3. (1982). "Synthesis of 2-methoxynaphthalene derivatives as potential anti-inflammatory agents". Farmaco Sci.
  4. (2010). "Time-Resolved Resonance Raman Studies on Proton-Induced Electron-Transfer Reaction from Triplet Excited State of 2-Methoxynaphthalene to Decafluorobenzophenone". The Journal of Physical Chemistry A.
  5. Mann, Frederick George. (1952). "Practical Organic Chemistry". Longmans, Green & Co.
  6. (1989). "Vogel’s textbook of practical organic chemistry". Pearson/Prentice Hall.
  7. (2016). "Organic Synthesis Experiments". Elsevier.
  8. (1973). "2-ACETYL-6-METHOXYNAPHTHALENE". Organic Syntheses.
  9. (March 1970). "Nonsteroidal antiinflammatory agents. I. 6-Substituted 2-naphthylacetic acids". Journal of Medicinal Chemistry.
  10. 林晓辉, 杨庆垂, & 淡勇德, CN111333494 (2023 to Wuhan Haixin Pharmaceutical Research Co ltd).
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