Effect of reaction conditions on the product distribution in the liquid-phase acid-catalyzed etherification of 2-naphthol with methanol

Abstract

Etherification of 2-naphthol with methanol to produce 2-naphthyl methyl ether was carried out in the presence of homogeneous acid catalysts. The effects of HClO 4 and H 2 SO 4 concentration, molar ratio of 2-naphthol/methanol, temperature, and inert atmosphere on the 2-naphthol conversion, on the 2naphthyl methyl ether selectivity, and on the product distribution were investigated.

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“…Recently, a detailed report on 2-naphthyl methyl ether selectivity depending on molar ratio of 2-naphthol/methanol, acid concentration, temperature, and inert atmosphere has appeared in the literature. 209 The t-butyl ether is a much underused alcohol protecting group, although it is one of the few ethers stable under strongly basic conditions. Its scarce employment in organic synthesis is probably due to the conditions required for its formation and removal.…”

“…Etherification of aromatics is a typical acid-catalyzed reaction and in particular etherification of 2-naphthol with methanol to produce the industrially important 2-naphthyl methyl ether is carried out in the presence of homogeneous HClO 4 solutions. Recently, a detailed report on 2-naphthyl methyl ether selectivity depending on molar ratio of 2-naphthol/methanol, acid concentration, temperature, and inert atmosphere has appeared in the literature …”