Boron trifluoride etherate → Methyl 1-hydroxy-7-methoxynaphthalene-2-carboxylate

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Reaction Steps

A suspension of 6.2 g (0.028 mole) of 1-hydroxy-7-methoxy-2-naphthalenecarboxylic acid in 75 ml of methanol under a nitrogen atmosphere was treated over 15 minutes with 15.0 ml (17.3 g; 0.12 mole) of boron trifluoride etherate. The mixture was stirred at reflux for 45 hours, cooled, and added slowly to 500 ml of ice cold 5% aqueous sodium bicarbonate solution. The precipitated product was filtered, and washed with water to yield 6.0 g (92% yield) of the ester, mp 80°-83°, suitable for further synthetic use. A sample purified by chromatography (silica gel, dichloromethane elution) was analytically pure, mp 79°-81° (a mp of 81°-82° is given by M. E. Alonso, A. W. Chitty, S. Pekerar, and M. de L. Borgo, J. Chem. Soc. Chem. Comm., 1542 (1984).

Provenance & Evidence