Ethanol → Phenylacetic Acid
Reaction equation
CN(C)[C:3](=[O:26])[CH2:4][C:5]1[CH:10]=[C:9](CC)[CH:8]=[CH:7][C:6]=1NC1C=CC(C)=C(C(F)(F)F)C=1F.CC[OH:30]>[OH-].[Na+]>[C:5]1([CH2:4][C:3]([OH:26])=[O:30])[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
A solution of the above 5-ethyl-2-(2′-fluoro-4′-methyl-3′-trifluoromethylanilino)phenylacetic acid N,N-dimethyl amide described in Example 3 (0.9 g, 2,4 mmol) in EtOH (25 mL) and 4N NaOH (12 mL) is heated to 80° C. overnight. After cooling, the reaction is concentrated under reduced pressure and diluted with ice cold EtOAc. The pH of the aqueous layer is adjusted to 1-2 with ice cold 2.5 N HCl. The separated organic layer is dried with Na2SO4 and concentrated to a solid. The solid is purified by trituration with an Et2O/hexane mixture to give the title acid, 5-ethyl-2-2′-fluoro-4′-methyl-3′-trifluoromethylanilino)phenylacetic acid.
Workup
- temperatureAfter cooling
- concentrationthe reaction is concentrated under reduced pressure
- additiondiluted with ice cold EtOAc
- dry with materialThe separated organic layer is dried with Na2SO4
- concentrationconcentrated to a solid
- customThe solid is purified by trituration with an Et2O/hexane mixture
Sources & evidence
- ORD record
- ord-047a578e29a3474b90a87bd5cebf9bbe
- Source dataset
- uspto-grants-2013_01
- Patent number
- US08362294B2
Reaction notes
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