2-Hydroxy-p-toluic acid → Methyl 2-methoxy-4-methylbenzoate
Reaction equation
O[C:2]1[CH:10]=[C:9](C)[CH:8]=[CH:7][C:3]=1[C:4](O)=O.[C:12](=[O:15])([O-])[O-:13].[Cs+].[Cs+].[CH3:18]I.CN(C)[CH:22]=[O:23]>>[CH3:18][O:13][C:12](=[O:15])[C:9]1[CH:8]=[CH:7][C:3]([CH3:4])=[CH:2][C:10]=1[O:23][CH3:22]Participants
5
Procedure
Commercially available 2-hydroxy-4-methylbenzoic acid (1.5 g, 10.0 mmol) and cesium carbonate (13.0 g, 40.0 mmol) were placed in a reaction vessel, and then N,N-dimethylformamide (40 ml) and methyl iodide (2.5 ml) were added thereto. The resulting mixture was stirred at room temperature for 5 hours. The reaction solution was filtered through celite and washed with ethyl acetate (300 ml). The filtrate was sequentially washed with water (100 ml) and a saturated aqueous sodium chloride solution (200 ml). Then, the filtrate was dried over anhydrous sodium sulfate, and concentrated under reduced pressure to yield 2-methoxy-4-methylbenzoic acid methyl ester (1.4 g) as a pale yellow oily material.
Workup
- filtrationThe reaction solution was filtered through celite
- washwashed with ethyl acetate (300 ml)
- washThe filtrate was sequentially washed with water (100 ml)
- dry with materialThen, the filtrate was dried over anhydrous sodium sulfate
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-cbd1d1d433794d8e9688c6df8498db7f
- Source dataset
- uspto-grants-2013_01
- Patent number
- US08362236B2
Reaction notes
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