Sodium Hydroxide → 4-(hydroxymethyl)-2-[(E)-2-[4-(trifluoromethyl)phenyl]ethenyl]-1,3-oxazole

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Reaction Steps

4-(Acetoxymethyl)-2-[(E)-2-[4-(trifluoromethyl)phenyl]-ethenyl]-1,3-oxazole (1556 g, 2.23 mol), 2N-aqueous sodium hydroxide solution (2.4 L, 4.8 mol) and activated carbon (47 g) were added to methanol (4.7 L), and the mixture was refluxed under stirring for 1 hour. The activated carbon and the insoluble material were removed by filtration under pressurization. The residue was washed with methanol/water (2:1) (470 ml). The washing solution was combined with the filtrate and the mixture was refluxed. Water (3.3 L) was added at the same temperature. After allowing to cool to room temperature and stirring, the mixture was stirred at the same temperature for 1 hour. The precipitated crystals were collected by filtration, washed with water (4.7 L) and dried under reduced pressure to give 4-(hydroxymethyl)-2-[(E)-2-[4-(trifluoromethyl)phenyl]ethenyl]-1,3-oxazole (568.5 g, 2.11 mol, yield 95%).

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