(4-Benzyloxy-6-fluoro-3-methyl-naphthalen-2-yl)-acetic acid methyl ester → (6-Fluoro-4-hydroxy-3-methyl-naphthalen-2-yl)-acetic acid methyl ester

Participants

Reaction Steps

A round-bottom flask was charged with (4-benzyloxy-6-fluoro-3-methyl-naphthalen-2-yl)-acetic acid methyl ester (11.7 g, 34.58 mmol) in ethanol (350 mL). Some heating was required in order to dissolve all of the starting material in ethanol. A full spatula scoop of 10% palladium on carbon was added into the reaction flask. The reaction mixture was stirred under hydrogen gas at atmospheric pressure overnight at room temperature. After this time, it appeared that approximately 750 mL hydrogen gas had been consumed, and TLC (1:3 ethyl acetate, hexanes) indicated that the starting material had been consumed. The reaction mixture was filtered through a bed of celite. The filtrate was concentrated to afford 7.91 g (92%) of (6-fluoro-4-hydroxy-3-methyl-naphthalen-2-yl)-acetic acid methyl ester, which was used in the next step without further purification. MS (ES−) cald. for C14H13FO3 [(M−H)−] 247, obsd. 247.1.

Provenance & Evidence