Sodium Hydroxide → 6-[4-({[3-(2,6-Dichlorophenyl)-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-1-naphthoic acid sodium salt

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A mechanically stirred suspension of 6-[4-({[3-(2,6-dichlorophenyl)-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-1-naphthalenecarboxylic acid (166 g, 0.31 mol) in methanol (500 mL) was treated with 1N sodium hydroxide (327 mL). The resulting solution was stirred at room temperature. The mixture was stirred 1 h and the resulting solid was collected by filtration, washed with acetone, hexane and then dried to give 151 g of the product as a white solid. 1H NMR (DMSO-d6): 9.04 (d, J=9 Hz, 1H), 8.00 (s, 1H), 7.78 (d, J=8 Hz, 1H), 7.72 (d, J=7 Hz, 1H), 7.66-7.61 (m, 5H), 7.53 (dd, J=7, 9 Hz, 1H), 7.37 (t, J=8 Hz, 1H), 6.88 (d, J=9 Hz, 2H), 4.85 (s, 2H), 3.46 (septet, J=7 Hz, 1H), 1.32 (d, J=7 Hz, 6H). ESI-LCMS m/z 532 (M+H)+.

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