Sodium Hydroxide → 4-(2-Fluoro-4-nitrophenyl)butanoic acid
Reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[CH2:11][CH2:12][CH2:13][C:14]([O:16]C)=[O:15].[OH-].[Na+]>CO.O>[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[CH2:11][CH2:12][CH2:13][C:14]([OH:16])=[O:15]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 21 °C
Procedure
To a solution of Methyl 4-(2-fluoro-4-nitrophenyl)butanoate (84) (43 mg, 0.18 mmol) in methanol (1 mL) and water (3 mL) was added sodium hydroxide (0.18 g, 4.50 mmol). The reaction mixture was stirred at 21° C. overnight. The reaction mixture was quenched with 1 N HCl solution and extracted with ethyl acetate (2×30 mL). The organic layer was dried over MgSO4, concentrated to give 4-(2-Fluoro-4-nitrophenyl)butanoic acid (82) (40 mg, 98%) and the residue was used without further purification.
Workup
- customThe reaction mixture was quenched with 1 N HCl solution
- extractionextracted with ethyl acetate (2×30 mL)
- dry with materialThe organic layer was dried over MgSO4
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-c71ece2c8d0646d6ac844b492fcb7d6f
- Source dataset
- uspto-grants-2014_03
- Patent number
- US08680291B2
Reaction notes
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