2-[1-(4-fluoro-phenyl)-meth-(E)-ylidene]-succinic acid → 6-Fluoro-4-hydroxy-2-naphthoic acid
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[C:9](\[CH2:13][C:14]([OH:16])=O)/[C:10]([OH:12])=[O:11])=[CH:4][CH:3]=1>FC(F)(F)S(O)(=O)=O>[F:1][C:2]1[CH:3]=[C:4]2[C:5](=[CH:6][CH:7]=1)[CH:8]=[C:9]([C:10]([OH:12])=[O:11])[CH:13]=[C:14]2[OH:16]Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 2-[1-(4-fluoro-phenyl)-meth-(E)-ylidene]-succinic acid (0.100 g, 0.44 mmol) in trifluoromethanesulfonic acid (0.5 mL) was stirred at room temperature for 16 hours. The resulting mixture was carefully poured into ice cold water with continuous stirring to obtain a solid precipitate, which was filtered, washed with water and dried under vacuum to yield 6-fluoro-4-hydroxy-naphthalene-2-carboxylic acid (0.065 g, 71%) as yellow solid. This crude product was pure enough to proceed to next step without further purification.