Reaktionsgleichung
[OH-].[K+].CO.O.C([O:9][CH:10]([CH:17]=[CH2:18])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)(=O)C>>[CH:17]([CH:10]([OH:9])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[CH2:18]Komponenten
Versuchsvorschrift
A second 12 L flask equipped with mechanical stirrer, condensor, and thermocouple was charged with 761.0 g (13.56 mol) KOH (potassium hydroxide), 3.5 L (86.6 mol) of MeOH (methanol), 1.1 L (58.38 mol) of water, and 703 g of vinylbenzyl acetate from the previous step producing a dark red-colored solution. The reaction was heated to reflux and followed by TLC, which indicated that the reaction was complete after 1 hour. The reaction mixture was cooled to room temperature and extracted twice with 4 L of diethyl ether. The ether layer was then washed with three times with 4 L of aqueous sodium chloride, then two times with 4 L of water. The ether layer was dried with MgSO4 (magnesium sulfate) and filtered. Ether was removed from the filtrate under reduced pressure to give a brown oil. (487.0 g, 91% yield) (94% overall). 1H NMR (DMSO-d6): δ 7.35 (m, 4H, aromatic), δ 6.70 (m, 1H, vinyl), δ 5.75 (d, 1H, vinyl), δ 5.25 (d, 1H, vinyl), δ 4.65 (d, 2H, benzyl).
Aufarbeitung
- customA second 12 L flask equipped with mechanical stirrer
- customproducing a dark red-colored solution
- temperatureThe reaction was heated
- temperatureto reflux
- extractionextracted twice with 4 L of diethyl ether
- washThe ether layer was then washed with three times with 4 L of aqueous sodium chloride
- dry with materialThe ether layer was dried with MgSO4 (magnesium sulfate)
- filtrationfiltered
- customEther was removed from the filtrate under reduced pressure
- customto give a brown oil
Quellen und Nachweise
- ORD-Eintrag
- ord-8f44880ce4d949818236db15fc13efff
- Quelldatensatz
- uspto-grants-2010_10
- Patentnummer
- US07815986B2
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