Water → 2,3,4,6-tetrafluorobenzoic Acid

HRID 2048078Notes

Reaction equation

HRID 2048078 reaction equation
[F:1][C:2]1[C:7]([F:8])=[C:6]([F:9])[CH:5]=[C:4]([F:10])[C:3]=1[CH2:11][OH:12].I([O-])(=O)(=O)=[O:14].[Na+].CC#N.O>[Ru](Cl)(Cl)Cl.C(Cl)(Cl)(Cl)Cl>[F:1][C:2]1[C:7]([F:8])=[C:6]([F:9])[CH:5]=[C:4]([F:10])[C:3]=1[C:11]([OH:14])=[O:12]

Participants

7

Reactant 4

HCID 962WaterHCID 6342AcetonitrileHCID 17750859(2,3,4,6-Tetrafluorophenyl)methanolHCID 23667635Sodium periodate

Product 1

HCID 27765912,3,4,6-tetrafluorobenzoic AcidYield 99%

Reagents, catalysts & solvents 2

HCID 61850Ruthenium trichlorideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

(2,3,4,6-Tetrafluorophenyl)methanol (1.50 g, 8.33 mmol), sodium periodate (8.91 g, 41.6 mmol) and ruthenium (III) chloride (345 mg, 1.67 mmol) was added to a mixture of MeCN (20 mL), water (10 mL) and carbon tetrachloride (20 mL). The reaction was stirred at room temperature for 6 hours, then filtered through arbocel (eluting with EtOAc) and the filtrate evaporated in vacuo. The resulting residue was purified by silica gel chromatography eluting with EtOAc to afford the title compound as a colourless oil (1.60 g, 99% yield):

Workup

  1. filtrationfiltered through arbocel (eluting with EtOAc)
  2. customthe filtrate evaporated in vacuo
  3. customThe resulting residue was purified by silica gel chromatography
  4. washeluting with EtOAc

Sources & evidence

ORD record
ord-ce77a98bf5954f408367c53f5ee30fa8
Source dataset
uspto-grants-2013_11
Patent number
US08592629B2

Reaction notes

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