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

HRID 1468325Notes

Reaction equation

HRID 1468325 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 give 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 calcd. for C12H8FO3 [(M−H)−] 219, obsd. 218.9.

Workup

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

Sources & evidence

ORD record
ord-f40580de6c004b13bc8c0b8a8b0e75df
Source dataset
uspto-grants-2015_04
Patent number
US09000044B2

Reaction notes

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