Dimethyl Sulfoxide → 3-Ethyl-2,4,5-trifluorobenzoic acid
Reaction equation
[C:1]([CH:4]([C:6]1[C:7]([F:20])=[C:8]([C:17]([OH:19])=[O:18])[C:9](=[C:13]([F:16])[C:14]=1[F:15])C(O)=O)C)(O)=O.CS(C)=O>C(N(CC)CC)C>[CH2:4]([C:6]1[C:7]([F:20])=[C:8]([CH:9]=[C:13]([F:16])[C:14]=1[F:15])[C:17]([OH:19])=[O:18])[CH3:1]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 140 °C
Procedure
A mixture of 4-(1-carboxyethyl)-3,5,6-trifluorophthalic acid (14.9 g, 47.9 mmol), dimethylsulfoxide(100 ml), and triethylamine (30 ml) was heated at 140° C. for 4 days, and the reaction mixture was concentrated to dryness. To the residue was added 1N Hcl (100 ml), and the solution was extracted with ether. The extract was washed with brine, dried over anhydrous sodium sulfate, and then evaporated to yield 9.27 g of the title compound as pale yellow crystals.
Workup
- concentrationthe reaction mixture was concentrated to dryness
- additionTo the residue was added 1N Hcl (100 ml)
- extractionthe solution was extracted with ether
- washThe extract was washed with brine
- dry with materialdried over anhydrous sodium sulfate
- customevaporated
Sources & evidence
- ORD record
- ord-8b6b44f87ac64b1c83b12c0fdb88249a
- Source dataset
- uspto-grants-1998_12
- Patent number
- US05849757
Reaction notes
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