Methyl iodide → 1,7-Dimethoxy-2-naphthalenecarboxylic acid

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Reaction Steps

A mixture of 3.7 g (0.016 mole) of 1-hydroxy-7-methoxy-2-naphthalenecarboxylic acid, methyl ester and 2.9 g (0.021 mole) of anhydrous potassium carbonate in 20 ml of N,N-dimethylformamide under a nitrogen atmosphere was treated with 3.0 ml (6.8 g; 0.048 mole) of iodomethane. The mixture was stirred at room temperature for 24 hours, and then added to 150 g of ice/water. The crude intermediate ester was separated by extracting with dichloromethane (3×50 ml). The combined organic layers were washed with water (2×50 ml), dried (anhydrous magnesium sulfate) and evaporated (vacuum).

Provenance & Evidence