Acetic Acid → Methyl 4-(2,2-dimethoxyethyl)-3-nitrobenzoate
Reaction equation
[CH3:1][O-:2].[Na+].[N+:4]([C:7]1[CH:8]=[C:9]([CH:14]=[CH:15][C:16]=1[C:17]#[C:18][Si](C)(C)C)[C:10]([O:12][CH3:13])=[O:11])([O-:6])=[O:5].[C:23]([OH:26])(=O)C>CO>[CH3:1][O:2][CH:18]([O:26][CH3:23])[CH2:17][C:16]1[CH:15]=[CH:14][C:9]([C:10]([O:12][CH3:13])=[O:11])=[CH:8][C:7]=1[N+:4]([O-:6])=[O:5]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a methanol solution of 2.92 g (54.1 mmol) of sodium methoxide was added 3.00 g (10.8 mmol) of methyl 3-nitro-4-trimethylsilylethynylbenzoate prepared above. The mixture was refluxed for 30 minutes. After cooling to 0° C., 5.52 g (54.1 mmol) of acetic acid was added to the reaction mixture and the solvent was then distilled off under reduced pressure. Ice water was poured onto the resulting residue followed by extraction three times with dichloromethane. After drying over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure and the residue was purified by silica gel column chromatography to give 2.40 g (82.4%) of methyl 4-(2,2-dimethoxyethyl)-3-nitrobenzoate.
Workup
- customprepared above
- temperatureThe mixture was refluxed for 30 minutes
- distillationthe solvent was then distilled off under reduced pressure
- additionIce water was poured onto the resulting residue
- extractionfollowed by extraction three times with dichloromethane
- dry with materialAfter drying over anhydrous magnesium sulfate
- distillationthe solvent was distilled off under reduced pressure
- customthe residue was purified by silica gel column chromatography
Sources & evidence
- ORD record
- ord-c8aa9f8562ab4b18b53824ca2cf81295
- Source dataset
- uspto-grants-2001_01
- Patent number
- US06169107A
Reaction notes
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