Hydrochloric Acid → Methyl 4-(hydroxymethyl)naphthalene-1-carboxylate

Participants

Reaction Steps

To a solution of methyl 4-((acetyloxy)methyl)-1-naphthalenecarboxylate (3.91 g, 15.1 mmol) in methanol (20 ml) was added 1N aqueous sodium hydroxide solution (15.1 ml, 15.1 mmol), and the mixture was stirred at room temperature for 5 min. 1N Hydrochloric acid was added to the reaction solution (20 ml) and the mixture was extracted with ethyl acetate (50 ml×2). The extract was washed with saturated brine, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1) to give methyl 4-(hydroxymethyl)-1-naphthalenecarboxylate (2.78 g, 85%).

Provenance & Evidence