Sodium Acetate → 3h-heptafluorotoluene

HRID 2107884Notes

Reaction equation

HRID 2107884 reaction equation
Cl[C:2]1[C:3]([F:15])=[C:4]([C:11]([F:14])([F:13])[F:12])[C:5]([F:10])=[C:6]([F:9])[C:7]=1[F:8].C([O-])(=O)C.[Na+].[H][H]>C(O)(=O)C.[Pd]>[F:10][C:5]1[C:6]([F:9])=[C:7]([F:8])[CH:2]=[C:3]([F:15])[C:4]=1[C:11]([F:14])([F:13])[F:12]

Participants

6

Reactant 3

HCID 517045Sodium AcetateHCID 27781953-Chloro-2,4,5,6-tetrafluorobenzotrifluorideHCID 178418361HCID 178418361, compound

Product 1

HCID 27825383h-heptafluorotolueneYield 96.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

252.5 g (1 mol) of 3-chloro-2,4,5,6-tetrafluorobenzotrifluoride (cf., for example, Zh. obshch. Khim., 37, 1686-1687 [1967]) and 86 g (1.05 mol) of sodium acetate in 1000 ml of glacial acetic acid are hydrogenated in the presence of 10 g of palladium-on-activated charcoal (5% strength) at a hydrogen pressure of 30 to 50 bar and 120° C. to constant pressure. For working-up, the catalyst is removed from the cold reaction mixture by filtration, and the residue is distilled. 210 g (96% of theory) of 2,3,4,6-tetrafluorobenzotrifluoride of boiling point 105°-106° C. and of refraction index nD20 =1.3770 are obtained.

Workup

  1. customthe catalyst is removed from the cold reaction mixture by filtration
  2. distillationthe residue is distilled

Sources & evidence

ORD record
ord-0dc4941088cf4234bd37cc0e84b6dfa1
Source dataset
uspto-grants-1990_06
Patent number
US04936892

Reaction notes

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