Potassium methoxide → 3-Methoxy-2-methyl-6-nitro-benzoic acid
Reaction equation
F[C:2]1[C:3]([CH3:14])=[C:4]([C:8]([N+:11]([O-:13])=[O:12])=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].[CH3:15][O-:16].[K+]>C1COCC1.CO>[CH3:15][O:16][C:2]1[C:3]([CH3:14])=[C:4]([C:8]([N+:11]([O-:13])=[O:12])=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 100 °C
Procedure
To a stirring solution of 3-Fluoro-2-methyl-6-nitro-benzoic acid (4.2 g, 21 mmol) in THF (40 mL) and methanol (40 mL) is added potassium methoxide in methanol (15 g, 63 mmol) and the solution is heated to 100° C. for 2 hours. The reaction mixture is cooled to room temperature and then the mixture is quenched with a 1N HCl solution and partitioned between ethyl acetate. The organic layer is washed with brine and then concentrated to give 3-Methoxy-2-methyl-6-nitro-benzoic acid (4.3 g) in quantitative yields. 1H-NMR (400 MHz, δ, ppm) CDCl3: 2.32 (s, 3H), 3.98 (s, 3H), 6.95 (d, 1H), 8.15 (d, 1H).
Workup
- temperatureThe reaction mixture is cooled to room temperature
- customthe mixture is quenched with a 1N HCl solution
- custompartitioned between ethyl acetate
- washThe organic layer is washed with brine
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-3f209a146c5b445d80373c9e577888c9
- Source dataset
- uspto-grants-2011_03
- Patent number
- US07910585B2
Reaction notes
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