Acetone → 6-Fluoro-4-hydroxy-3-methyl-naphthalene-2-carboxylic acid methyl ester

Participants

Reaction Conditions

Reaction Steps

A heterogeneous mixture of potassium carbonate (46 g, 0.33 mol), water (260 mL), and acetone (260 mL) was added in three portions to a 0° C. solution of 4-acetoxy-6-fluoro-3-methyl-naphthalene-2-carboxylic acid methyl ester (18.4 g, 0.066 mol) in methanol (1 L). The resulting mixture was stirred at 0° C. for 15 minutes, then warmed to room temperature and stirred at room temperature for 1 hour. The reaction mixture was concentrated in vacuo. The remaining oily suspension was diluted with ethyl acetate and washed with 1 N aqueous HCl. The organic phase was dried (MgSO4), filtered, and concentrated to yield 9.64 g (62%) of 6-fluoro-4-hydroxy-3-methyl-naphthalene-2-carboxylic acid methyl ester as a yellowish tan solid. HRMS (ES−) cald. for C13H11FO3 [(M−H)−] 233.0619, obsd. 233.0619.

Provenance & Evidence