Methanol → Methyl 3-(4-acetyl-2-methylphenyl)acrylate
Reaktionsgleichung
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]=[CH:11][C:12]([OH:14])=[O:13])=[C:6]([CH3:15])[CH:5]=1)(=[O:3])[CH3:2].S(=O)(=O)(O)O.O.[CH3:22]O>>[C:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]=[CH:11][C:12]([O:14][CH3:22])=[O:13])=[C:6]([CH3:15])[CH:5]=1)(=[O:3])[CH3:2]Komponenten
Versuchsvorschrift
The obtained 3-(4-acetyl-2-methylphenyl)acrylic acid (657 mg, 3.22 mmol) was dissolved in methanol (20 mL). Concentrated sulfuric acid (250 μL) was added to the solution. The mixture was refluxed for 2 hours, and cooled to room temperature. Water (50 mL) was added to the solution. Methanol was removed under reduced pressure. The solution was extracted with ethyl acetate, washed with saturated aqueous sodium bicarbonate solution and saturated brine. The organic layer was dried with anhydrous sodium sulfate. The solvent was removed under reduced pressure. The obtained residue was purified by silica gel column chromatography with hexane/ethyl acetate (9:1, v/v) to give the desired compound (665 mg) as yellow crystalline product (yield 95%).
Aufarbeitung
- temperatureThe mixture was refluxed for 2 hours
- customMethanol was removed under reduced pressure
- extractionThe solution was extracted with ethyl acetate
- washwashed with saturated aqueous sodium bicarbonate solution and saturated brine
- dry with materialThe organic layer was dried with anhydrous sodium sulfate
- customThe solvent was removed under reduced pressure
- customThe obtained residue was purified by silica gel column chromatography with hexane/ethyl acetate (9:1
Quellen und Nachweise
- ORD-Eintrag
- ord-d24e7d53c3a84fcdac73aeaf6f8c3599
- Quelldatensatz
- uspto-grants-2013_03
- Patentnummer
- US08404726B2
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