Water → Methyl 6-hydroxy-2-naphthoate

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Reaction Steps

6-Methoxy-naphthalene-2-carboxylic acid methyl ester (0.68 g, 3.13 mmol) is stirred in dichloromethane (50 mL) in an ice/water bath. Aluminum trichloride (1.67 g, 12.5 mmol) is added followed by ethane thiol (1.2 mL, 15.7 mmol). The mixture is stirred at room temperature 2 hr. Water (25 mL) is added and the product is extracted into ethyl acetate (2×75 mL). The combined extracts are concentrated, and the residue is purified via silica gel chromatography eluting with 8:2 hexanes:ethyl acetate to afford the title compound as a white solid, 0.432 g, 69%. MS M++1 203. The structure is confirmed by 1H NMR spectroscopy.

Provenance & Evidence