2-Naphthalenecarboxylic acid, 1-hydroxy-, methyl ester → Methyl 1-(2,2,2-trifluoroethoxy)naphthalene-2-carboxylate

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Reaction Steps

A mixture containing 20.2 g. (0.1 mole) of methyl 1-hydroxy-2-naphthoate, 29 g. (0.125 mole) of 2,2,2-trifluoroethyl trifluoromethanesulfonate, 20 g. (0.2 mole) of anhydrous potassium bicarbonate and 200 ml. of dry acetone is refluxed for three days. Acetone is removed by distillation (steam bath). The residue is cooled and diluted with water. The resulting white solid is collected by filtration and washed successively with cold dilute sodium hydroxide solution and water. The solid is further purified by several rcrystallizations from aqueous alcohol followed by sublimation, (oil bath, 60°-75°/0.2 mm. Hg.) to give white solid, m.p. 69.5°-70.5°.

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