Sodium Iodide → Methyl 4-(2-naphthyloxymethyl)benzoate

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Reaction Steps

To a solution of 2-naphthol (26 g) in DMF (300 ml) is added sodium hydride (7.2 g of 60% dispersion). When gas evolution ceases, methyl 4-(chloromethyl)benzoate (32.9 g) and sodium iodide (10 g) are added, and the reaction mixture is stirred at 140° for 3 hr, and at 90° for an additional 18 hr. The mixture is cooled, poured into 2000 ml ice water, and the product extracted with 1:1 ether-hexane. The extracts are dried, filtered, and concentrated, providing methyl 4-(2-naphthyloxymethyl)benzoate as a tan solid (42.8 g, 91%). The ester is reduced with lithium aluminum hydride in THF in the usual fashion, and the resulting benzyl alcohol is converted by Swern oxidation (oxalyl chloride /DMSO) to 4-(2-naphthyloxymethyl)benzaldehyde. By the method of example 1, this is converted to the title compound, obtained as a pale yellow solid, mp. 213°-215° after recrystallization from hexane-ethyl acetate.

Provenance & Evidence