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

HRID 1261425Notes

Reaction equation

HRID 1261425 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 100%

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, 119 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 (28g, >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-464b2e0897d14cc79774bb3bf44bd604
Source dataset
uspto-grants-2013_06
Patent number
US08470884B2

Reaction notes

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