[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[C:13]([C:14]([O:16]CC)=[O:15])=[C:12]([CH3:19])[O:11][N:10]=1.[OH-].[Na+].CCOCC.Cl>CO.O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[C:13]([C:14]([OH:16])=[O:15])=[C:12]([CH3:19])[O:11][N:10]=1
The reaction mixture of ethyl 3-(2-methoxyphenyl)-5-methylisoxazole-4-carboxylate (12.85 g, 49.2 mmol) and sodium hydroxide (9.84 g, 246 mmol) in MeOH (100 mL) and Water (10 mL) in a 500-mL round bottom flask was stirred at 65° C. for 20 hours. The MeOH was removed in vacuo, then the concentrated reaction mixture was transferred to a 500-mL separatory funnel with 150 mL of water and 100 mL of ether. The organic layer was discarded. The aqueous layer was acidified by adding concentrated HCl (26 mL). The product precipitated and was separated by filtration and dried under high vacuum to give 10.63 g (93%, theoretical yield 11.47 g). 1H NMR (400 MHz, CD3OD) δ 2.69 (s, 3H, CH3), 3.77 (s, 3H, OCH3), 7.00-7.07 (m, 2H, aryl), 7.32-7.34 (m, 1H, aryl), 7.43-7.48 (m, 1H, aryl).
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