Methanol → 1-Hydroxy-4-(beta-methanesulfonamidoethoxy)-2-naphthoic acid

Participants

Reaction Steps

41 g (0.2 mole) of 1,4-dihydroxynaphthoic acid was dissolved in 200 ml DMF, into which was added dropwise 80 g of a 28% methanol solution of sodium methoxide (0.4 mole) and bubbling nitrogen therethrough at room temperature. Then, while controlling the reaction temperature between 35°-40° C., 25.2 g (0.16 mole) of β-methanesulfonamidoethyl chloride was added and the mixture was stirred for 1 hour. Finally, the solution was poured into a mixture of 100 ml of concentrated (36%) hydrochloric acid and 500 ml of water to separate a crystalline product, which was filtered. The crystalline product was purified by refluxing with methanol and, thus, 20.8 g of 1-hydroxy-4-(β-methanesulfonamidoethoxy)-2-naphthoic acid was obtained with a yield of 40%.

Provenance & Evidence