Sodium Hydroxide → 3-Ethoxy-6-hydroxy-2-methylbenzoic acid
Reaction equation
Br[C:2]1[C:7]([C:8]([O:10]C)=[O:9])=[C:6]([CH3:12])[C:5]([O:13][CH2:14][CH3:15])=[CH:4][CH:3]=1.[OH-].[Na+].C(=O)(O)[O-:19].[Na+].CN[C@@H]1CCCC[C@H]1NC>CS(C)=O.O.S([O-])([O-])(=O)=O.[Cu+2].C(OCC)(=O)C>[CH2:14]([O:13][C:5]1[C:6]([CH3:12])=[C:7]([C:2]([OH:19])=[CH:3][CH:4]=1)[C:8]([OH:10])=[O:9])[CH3:15]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 4
Conditions
- Temperature
- 95 °C
Procedure
A solution of methyl 6-bromo-3-ethoxy-2-methylbenzoate (114c, 0.298 g, 1.09 mmol) in DMSO (4 mL) was treated with 10M NaOH (1.0 mL, 10 mmol) and heated at 95° C. After 1 hour, the ester was hydrolyzed. The reaction mixture was cooled to room temperature and sodium bicarbonate (0.850 g, 10.1 mmol) and water (3 mL) were added. The suspension was sonicated until homogeneous. A solution of copper(II) sulfate (0.0348 g, 0.218 mmol) and trans-N,N′-dimethylcyclohexane-1,2-diamine (0.071 mL, 0.44 mmol) in water (2.0 mL) was added. The reaction mixture was heated at 95° C. for 1 hour. The reaction mixture was cooled to room temperature, poured into ethyl acetate, and washed with 1N HCl and brine. The organic layer was dried over Na2SO4 and concentrated under vacuum to give 3-ethoxy-6-hydroxy-2-methylbenzoic acid (114d, 0.168 g, 79% yield) as a salmon colored solid.
Workup
- temperatureThe reaction mixture was cooled to room temperature
- customThe suspension was sonicated until homogeneous
- temperatureThe reaction mixture was heated at 95° C. for 1 hour
- temperatureThe reaction mixture was cooled to room temperature
- washwashed with 1N HCl and brine
- dry with materialThe organic layer was dried over Na2SO4
- concentrationconcentrated under vacuum
Sources & evidence
- ORD record
- ord-02955aef4c42479d9c7cf881469b90a7
- Source dataset
- uspto-grants-2015_05
- Patent number
- US09040515B2
Reaction notes
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