Dimethylacetamide → 2,3,5,6-Tetrafluorobenzoic Acid

HRID 482145

Reaction equation

HRID 482145 reaction equation
CN(C)C(=O)C.[F:7][C:8]1[C:16]([F:17])=[C:15](C(O)=O)[C:14]([F:21])=[C:13]([F:22])[C:9]=1[C:10]([OH:12])=[O:11]>O>[F:7][C:8]1[C:16]([F:17])=[CH:15][C:14]([F:21])=[C:13]([F:22])[C:9]=1[C:10]([OH:12])=[O:11]

Participants

4

Reactant 2

HCID 31374DimethylacetamideHCID 695492,3,5,6-Tetrafluoroterephthalic acid

Product 1

HCID 5675332,3,5,6-Tetrafluorobenzoic AcidYield 98%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
20 °C

Procedure

N,N-Dimethylacetamide (14.0 parts) and 2,3,5,6-tetrafluoroterephthalic acid (2.91 parts) was heated at 70° C. for 4 hours before cooling to 20° C. adding water (7 parts) and cooling to 5° C. The precipitated solid was collected by filtration and washed with cold water and dried, the aqueous filtrates were evaporated under vacuum and the resultant solids combined to give 2,3,5,6-tetrafluorobenzoic acid (98%). 1,2,4,5-tetrafluorobenzene (2%) was also formed.

Workup

  1. temperaturecooling to 5° C
  2. filtrationThe precipitated solid was collected by filtration
  3. washwashed with cold water
  4. customdried
  5. customthe aqueous filtrates were evaporated under vacuum

Sources & evidence

ORD record
ord-c0a4bb5b3740452caefe96c7cf33b70b
Source dataset
uspto-grants-1998_08
Patent number
US05792887

Linked notes

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