Ethyl acetate hexane → (6-Fluoro-4-hydroxy-naphthalen-2-yl)-acetic acid methyl ester

Participants

Reaction Steps

To a stirred solution of (4-benzyloxy-6-fluoro-naphthalen-2-yl)-acetic acid methyl ester (18.5 g, 57.0 mmol) in methanol (200 mL) was added 10% palladium on carbon (2.78 g). The resulting mixture was vigorously stirred under a balloon of hydrogen overnight. The reaction mixture was filtered through celite. The filtrate was concentrated in vacuo to obtain a crude product. Silica gel chromatography (10% ethyl acetate-hexane) afforded (6-fluoro-4-hydroxy-naphthalen-2-yl)-acetic acid methyl ester (10.24 g, 76%) as a white solid. MS cald. for C13H12FO3 [(M+H)+]: 235, obsd. 235.2.

Provenance & Evidence