Triethylamine → 2,4,5-Trifluoro-3-methylbenzoic acid

HRID 1458002Notes

Reaction equation

HRID 1458002 reaction equation
C([CH2:4][C:5]1[C:6]([F:19])=[C:7]([C:16]([OH:18])=[O:17])[C:8](=[C:12]([F:15])[C:13]=1[F:14])C(O)=O)(O)=O.C(N(CC)CC)C>CS(C)=O>[F:19][C:6]1[C:5]([CH3:4])=[C:13]([F:14])[C:12]([F:15])=[CH:8][C:7]=1[C:16]([OH:18])=[O:17]

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 9795630HCID 9795630, compound

Product 1

HCID 118055142,4,5-Trifluoro-3-methylbenzoic acidYield 60%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
140 °C

Procedure

To 304.35 g of 4-carboxymethyl-3,5,6-trifluorophthalic acid dissolved in 1.5 liters of dimethyl sulfoxide was added 0.5 liter of triethylamine, followed by 64 hours of stirring at 140° C. After cooling to room temperature, dimethyl sulfoxide was evaporated. The resulting residue was mixed with 1 liter of 1N hydrochloric acid and extracted with ether (1 liter×3). The organic layer was washed with 1 liter of water and 1 liter of saturated brine, and then dried over sodium sulfate. By evaporating the solvent, 177.94 g (0.64 mol, 60%) of the title compound was obtained as a partially purified product.

Workup

  1. temperatureAfter cooling to room temperature
  2. customdimethyl sulfoxide was evaporated
  3. additionThe resulting residue was mixed with 1 liter of 1N hydrochloric acid
  4. extractionextracted with ether (1 liter×3)
  5. washThe organic layer was washed with 1 liter of water and 1 liter of saturated brine
  6. dry with materialdried over sodium sulfate
  7. customBy evaporating the solvent

Sources & evidence

ORD record
ord-e9ae12401d284f98b2cd6eef6ebaf88f
Source dataset
uspto-grants-1998_12
Patent number
US05849757

Reaction notes

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