Reaktionsgleichung
[C:1]([C:3]1[CH:9]=[C:8]([OH:10])[C:7]([C:11]#[N:12])=[CH:6][C:4]=1[OH:5])#[N:2].[CH2:13](Br)[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].C(=O)([O-])[O-].[K+].[K+].Cl>C(O)C.CN(C=O)C>[CH2:13]([O:10][C:8]1[C:7]([C:11]#[N:12])=[CH:6][C:4]([OH:5])=[C:3]([C:1]#[N:2])[CH:9]=1)[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]Komponenten
Reaktionsbedingungen
- Temperatur
- 120 °C
Versuchsvorschrift
In a 300 ml-reaction vessel, 350 g (2.19×10-1M) of 2,5-dicyanohydroquinone, 23.8 g (1.44×10-1M) of n-hexylbromide, 20.0 g (1.45×10-1M) of potassium carbonate and 180 ml of DMF were placed, followed by stirring for 3 hours at 120° C. After the reaction, the reaction mixture was cooled and poured into 500 ml of 4N-hydrochloric acid, followed by extraction with ethyl acetate. The organic layer was washed with water and dried with anhydrous magnesium sulfate, followed by distilling-off of the solvent. The resultant residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=2/1) to obtain 17.6 g of a crude product. The crude product was dissolved in ethanol and treated with activated carbon, followed by recrystallization from ethanol to obtain 8.2 g of 4-hexyloxy2,5-dicyanophenol (Yield: 22.9%).
Aufarbeitung
- customAfter the reaction
- temperaturethe reaction mixture was cooled
- extractionfollowed by extraction with ethyl acetate
- washThe organic layer was washed with water
- dry with materialdried with anhydrous magnesium sulfate
- customThe resultant residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=2/1)
- customto obtain 17.6 g of a crude product
- additiontreated with activated carbon
- customfollowed by recrystallization from ethanol
Quellen und Nachweise
- ORD-Eintrag
- ord-6ffb40ec7d9641208bf07915355dfcfd
- Quelldatensatz
- uspto-grants-1999_01
- Patentnummer
- US05858269
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