2-Methoxynaphthalene

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, 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.

The Friedel–Crafts acylation with propionyl chloride gives 2-propionyl-6-methoxynaphthalene . 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, which is a critical compound for manifold reasons.