2-[1-(4-fluoro-phenyl)-meth-(E)-ylidene]-succinic acid → 6-Fluoro-4-hydroxy-2-naphthoic acid

HRID 2363805Notes

Reaction equation

HRID 2363805 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

HCID 821588632-[1-(4-fluoro-phenyl)-meth-(E)-ylidene]-succinic acid

Product 1

HCID 823722636-Fluoro-4-hydroxy-2-naphthoic acidYield 71.7%

Reagents, catalysts & solvents 1

HCID 62406Trifluoromethanesulfonic acidSolvent

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.

Workup

  1. additionThe resulting mixture was carefully poured into ice cold water
  2. customto obtain a solid precipitate, which
  3. filtrationwas filtered
  4. washwashed with water
  5. customdried under vacuum

Sources & evidence

ORD record
ord-e16fbc208e1e4561ad5f9a4e0a736a21
Source dataset
uspto-grants-2014_04
Patent number
US08691993B2

Reaction notes

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