Methoxynaphthalene chemistry

The latter result is particularly interesting because it contrasts so vividly with the chemistry observed in homogeneous solution. With a homogeneously dispersed single electron photoacceptor, 1-methoxynaphthalene gives the same product as that formed in Ti02, but 1-methylnaphthalene gives a completely different product, that derived from exclusive side chain activation by radical cation deprotonation, eq. 94 (290) ... 

Optimal operating conditions and catalysts Acetylation of phenyl ethers was generally carried out in the absence of solvents, which makes easier the recovery of the acetylated product from the reaction mixture. On the other hand, because of the high melting point of substrate and acetylated products, solvents were always used in the acetylation of 2-methoxynaphthalene. Flow reactors (e.g. fixed bed tubular reactors), in which the detrimental effect of competitive adsorption of substrate and products on the acetylation yield is lower than in the batch reactors, should be preferred. However although the set up of fixed bed reactors for liquid phase reactions is relatively simple, their substitution to the batch reactors, which are the only system used in academic organic chemistry, remains essentially limited to commercial units. 

M. L. Penninger, J. M. M. Kolmschate, Chemistry of methoxynaphthalene in supercritical water, in Supercritical Fluid Science and Technology, K. P. Johnston, J. M. L. Penninger (Eds.), American Chemical Society, 1989. 

The Friedel-Crafts acylation of aromatic ethers has attracted considerable interest in organic synthesis and in industrial chemistry because of the widespread application of the corresponding ketones as valuable intermediates in fine chemistry [39-43]. An example is the selective acetylation of 2-methoxynaphthalene at the carbon in position 6 owing to the great interest in 2-methoxy-6-acetylnaphthalene, an intermediate in the preparation of the anti-inflammatory drug (S)-Naproxen [44,45]. 

A recent example of the tolerance of this chemistry to steric bulk was reported by Tanaka (Scheme 4.361) [529], Treatment of l-ethynyl-2-methoxynaphthalene with BuLi at low temperatures followed by addition of the chlorophosphonate afforded the alkynylphosphonate in moderate yields (68%) after purification by column chromatography. 

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