Boron tribromide → 1-Hydroxy-4-naphthoic acid

Beteiligte Stoffe

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Under nitrogen, 4-methoxy-1-naphthoic acid (4.33 g) in dichloromethane (45 ml) was added boron tribromide (1M in dichloromethane, 63 ml) dropwise at 0° C., and the mixture was stirred at the same temperature for 2 hours. The resulting mixture was poured into ice-cold water and the precipitate was collected by filtration. The filter cake was added to the mixture of water and ethyl acetate, and then adjusted to pH 9 with 1N sodium hydroxide. After separation, the organic layer was dried over anhydrous magnesium sulfate and evaporated in vacuo to afford 4-hydroxy-1-naphthoic acid (2.19 g) as a colorless powder.

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