Potassium Carbonate → HCID 69487859, compound

HRID 1594022Notes

Reaction equation

HRID 1594022 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:10](=O)[O:11][C:12](=[O:14])[CH:13]=2)=[CH:5][CH:4]=1.FC(F)(F)C1C=CC(CC#[N:28])=CC=1.O.C(O)(=O)C=O.C(=O)([O-])[O-].[K+:41].[K+]>CO>[K+:41].[C:10]([C:9]([C:6]1[CH:7]=[CH:8][C:3]([C:2]([F:17])([F:16])[F:1])=[CH:4][CH:5]=1)=[CH:13][C:12]([O-:11])=[O:14])#[N:28]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 753594-(Trifluoromethyl)phenylacetonitrileHCID 15620607Glyoxylic acid, monohydrateHCID 23577229HCID 23577229, compound

Product 1

HCID 69487859HCID 69487859, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-(4-Trifluoromethyl-phenyl)-furan-2,5-dione. A mixture of 4-(trifluoromethyl)phenylacetonitrile (9.26 g, 50 mmol), glyoxylic acid monohydrate (6.9 g, 75 mmol), and potassium carbonate (17 g, 125 mmol) in methanol (100 mL) was stirred at room temperature for 3-5 h. The resulting thick solid precipitate was filtered and washed with dichloromethane. This solid was suspended in 250 mL of water, stirred overnight, and filtered and air-dried to provide 3-cyano-3-(4-trifluoromethyl-phenyl)-acrylic acid potassium salt. This was dissolved in 88% formic acid (ca. 200 mL) containing concentrated sulfuric acid (15 mL). This mixture was heated at reflux for 2-3 h and cooled and poured into ice water. The resulting precipitate was collected by filtration, washed with water, and air dried to provide the title compound. 1H NMR (DMSO-d6) δ 7.94 (s, 1H), 7.97 (d, J=8.2 Hz, 2H), 8.24 (d, J=8.2 Hz, 2H).

Workup

  1. filtrationThe resulting thick solid precipitate was filtered
  2. washwashed with dichloromethane
  3. stirringstirred overnight
  4. filtrationfiltered
  5. customair-dried

Sources & evidence

ORD record
ord-c99c05b39b8e4a84afa4edd263723d1d
Source dataset
uspto-grants-2007_11
Patent number
US07300932B2

Reaction notes

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