Dimethylformamide → Methyl 3-isopropyl-2-methoxybenzoate
Reaction equation
O[C:2]1[C:10]([CH:11]([CH3:13])[CH3:12])=[CH:9][CH:8]=[CH:7][C:3]=1C(O)=O.[C:14](=[O:17])([O-])[O-:15].[K+].[K+].I[CH3:21].[S].CN([CH:26]=[O:27])C>>[CH3:21][O:15][C:14](=[O:17])[C:8]1[CH:7]=[CH:3][CH:2]=[C:10]([CH:11]([CH3:13])[CH3:12])[C:9]=1[O:27][CH3:26]Participants
Procedure
28 g (156.25 mmol) of 2-hydroxy-3-isopropylbenzoic acid is dissolved in 280 ml of DMF and added in drops to a mixture of 47.5 g of potassium carbonate in 274 ml of DMF. After one more hour of stirring at room temperature, 21.4 ml (343.76 mmol) of iodomethane is added in drops, and the mixture is stirred for one day at room temperature. After acidification with 10% sulfur acid to pH 3-4 (ice bath cooling), the reaction mixture is extracted four times with 500 ml each of methyl tert-butyl ether. The combined organic extracts are washed with water and with brine and dried on sodium sulfate. After the desiccant is filtered off, the solvent is spun off, and the residue is chromatographed several times on silica gel (mobile solvent methyl tert-butyl ether/hexane). 25.59 g (79.02%) of the desired compound is isolated.
Workup
- stirringthe mixture is stirred for one day at room temperature
- extractionthe reaction mixture is extracted four times with 500 ml each of methyl tert-butyl ether
- washThe combined organic extracts are washed with water and with brine
- customdried on sodium sulfate
- filtrationAfter the desiccant is filtered off
- customthe residue is chromatographed several times on silica gel (mobile solvent methyl tert-butyl ether/hexane)
Sources & evidence
- ORD record
- ord-42ad8d8254144170879ec9bc43655ac3
- Source dataset
- uspto-grants-2009_12
- Patent number
- US07638515B2
Reaction notes
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