Water → Methyl 3-hydroxy-1-(methoxymethoxy)-2-naphthoate

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Reaction Steps

To a solution of 1,3-dihydroxy-2-naphthoic acid methyl ester 109 mg (0.53 mmol) in DMF (2 mL) was added triethylamine (200 μL, 1.43 mmol) and chloromethyl methyl ether (MOMCl) (125 μL, 1.65 mmol). The mixture was stirred at ambient temperature for 16 hours, poured into water (10 mL) and extracted with diethyl ether (2×5 mL). The combined ether layers were washed with 1M HCl (1×3 mL), brine (1×5 mL), dried (MgSO4), filtered, and concentrated under reduced pressure to an oil. The oil was purified on silica gel eluting with 20% ethyl acetate/hexanes to provide the titled compound (83 mg, 60%).

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