Ethanol → Ethyl 3-hydroxy-2-methylbenzoate
Reaction equation
[OH:1][C:2]1[C:3]([CH3:11])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].S(=O)(=O)(O)O.[CH2:17](O)[CH3:18]>O>[OH:1][C:2]1[C:3]([CH3:11])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([O:7][CH2:17][CH3:18])=[O:6]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 90 °C
Procedure
To a solution of 3-hydroxy-2-methylbenzoic acid (2.0 g, 13 mmol) in absolute ethanol (20 mL) was added sulfuric acid (2.0 mL, 37 mmol). The resulting mixture was stirred at 90° C. for 16 hours. The reaction was cooled to room temperature then diluted with water (20 mL). The mixture was extracted with dichloromethane (2×50 mL). The combined organic layers were washed with brine (50 mL), dried over magnesium sulfate and concentrated under vacuum to give ethyl 3-hydroxy-2-methylbenzoate (116a, 2.4 g, 99% yield) as yellow oil.
Workup
- temperatureThe reaction was cooled to room temperature
- extractionThe mixture was extracted with dichloromethane (2×50 mL)
- washThe combined organic layers were washed with brine (50 mL)
- dry with materialdried over magnesium sulfate
- concentrationconcentrated under vacuum
Sources & evidence
- ORD record
- ord-373fba7cfeee4825a2634b18c4bd8dc4
- Source dataset
- uspto-grants-2015_05
- Patent number
- US09040515B2
Reaction notes
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