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

HRID 2359310Notes

Reaction equation

HRID 2359310 reaction equation
CC#N.O.[F:5][C:6]1[C:11]([F:12])=[C:10]([F:13])[CH:9]=[C:8]([F:14])[C:7]=1[CH2:15][OH:16].I([O-])(=O)(=O)=[O:18].[Na+]>[Ru](Cl)(Cl)Cl.C(Cl)(Cl)(Cl)Cl>[F:5][C:6]1[C:11]([F:12])=[C:10]([F:13])[CH:9]=[C:8]([F:14])[C:7]=1[C:15]([OH:18])=[O:16]

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 100%

Reagents, catalysts & solvents 2

HCID 61850Ruthenium trichlorideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

To a mixture of MeCN (20 mL), water (10 mL), carbon tetrachloride (20 mL) was added (2,3,4,6-tetrafluorophenyl)methanol (1.50 g, 8.33 mmol), sodium periodate (8.91 g, 41.6 mmol) and finally ruthenium (III) chloride (345 mg, 1.67 mmol). The reaction was stirred at room temperature for 6 hours before the mixture was filtered through Arbocel washing the pad thouroughly with ethyl acetate and directly purified by silica gel column chromatography eluting with ethyl acetate to afford the title compound as a colourless oil (1.60 g, 100%).

Workup

  1. filtrationwas filtered through Arbocel washing the pad thouroughly with ethyl acetate
  2. customdirectly purified by silica gel column chromatography
  3. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-d527955a3e3742e0ad04679ac4f90de7
Source dataset
uspto-grants-2014_04
Patent number
US08685977B2

Reaction notes

Loading…