Water → 6-Fluoro-4-hydroxy-3-methyl-naphthalene-2-carboxylic acid

HRID 2363816Notes

Reaction equation

HRID 2363816 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[C:9](\[CH:13]([CH3:17])[C:14]([OH:16])=O)/[C:10]([OH:12])=[O:11])=[CH:4][CH:3]=1.O>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])[C:13]([CH3:17])=[C:14]2[OH:16]

Participants

4

Reactant 2

HCID 962WaterHCID 895403562-[1-(4-fluoro-phenyl)-meth-(E)-ylidene]-3-methyl succinic acid

Product 1

HCID 866838256-Fluoro-4-hydroxy-3-methyl-naphthalene-2-carboxylic acidYield 107.8%

Reagents, catalysts & solvents 1

HCID 62406Trifluoromethanesulfonic acidSolvent

Procedure

A solution of 2-[1-(4-fluoro-phenyl)-meth-(E)-ylidene]-3-methyl succinic acid (28 g, 118 mmol) in trifluoromethanesulfonic acid (140 mL) was stirred at room temperature for 16 h. The resulting mixture was carefully poured into ice cooled water with continuous stirring to obtain a solid precipitate, which was filtered, washed with water and dried in vacuo to yield 6-fluoro-4-hydroxy-3-methyl-naphthalene-2-carboxylic acid (28 g, >100% crude) as yellow solid. This crude product was used in the next step without further purification. MS cald. for C12H8FO3 [(M−H)−] 219, obsd. 218.9.

Workup

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

Sources & evidence

ORD record
ord-a055b8034a1b4bdf8ea989a9013407aa
Source dataset
uspto-grants-2014_04
Patent number
US08691993B2

Reaction notes

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