p-Toluenesulfonic acid → 1,5-Dimethyl-8-oxa-bicyclo[3.2.1]oct-6-ene-2,4-dione
Reaktionsgleichung
C[O:2][C:3]1(OC)[C:9]2([CH3:11])[O:10][C:6]([CH3:12])([CH:7]=[CH:8]2)[C:5](=[O:13])[CH2:4]1.C1(C)C=CC(S(O)(=O)=O)=CC=1.CCCCCC.C(OCC)(=O)C>CC(C)=O.O>[CH3:11][C:9]12[O:10][C:6]([CH3:12])([CH:7]=[CH:8]1)[C:5](=[O:13])[CH2:4][C:3]2=[O:2]Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Versuchsvorschrift
1.61 g (7.59 mmol) of 4,4-dimethoxy-1,5-dimethyl-8-oxa-bicyclo[3.2.1]oct-6-en-2-one and 0.432 g (2.28 mmol) of p-toluenesulfonic acid are dissolved in a 2:1 mixture of acetone and water and heated for 50 minutes at a temperature of 70° C. (TLC monitoring: hexane/ethyl acetate 9:1). The acetone is then removed under reduced pressure. The aqueous phase is then adjusted to pH 9 with saturated sodium hydrogen carbonate solution and extracted three times with ethyl acetate to remove neutral components. The aqueous phase is then adjusted to pH 5 with dilute hydrochloric acid and extracted three times with fresh ethyl acetate. The organic phase is dried over sodium sulfate and concentrated by evaporation under reduced pressure, there being obtained 1.04 g (82.5%) of technically pure 1,5-dimethyl-8-oxa-bicyclo[3.2.1]oct-6-ene-2,4-dione in the form of a yellowish product, which can be used without further purification in the next reaction step to form compounds of formula I.
Aufarbeitung
- customThe acetone is then removed under reduced pressure
- extractionextracted three times with ethyl acetate
- customto remove neutral components
- extractionextracted three times with fresh ethyl acetate
- dry with materialThe organic phase is dried over sodium sulfate
- concentrationconcentrated by evaporation under reduced pressure, there
Quellen und Nachweise
- ORD-Eintrag
- ord-0a6879ce32d44e0e9323f14825e62126
- Quelldatensatz
- uspto-grants-2010_08
- Patentnummer
- US07776888B2
Notizen zur Reaktion
Wird geladen…