Reaktionsgleichung
[CH:1]([OH:6])(O)[CH2:2][CH2:3][CH3:4].[O-:7][CH2:8][CH2:9][CH2:10][CH3:11].[K+].Cl[CH2:14][CH:15]=[CH:16][C:17]1C=CC=C[CH:18]=1>>[OH:7][CH2:8][CH2:9][CH2:10][CH2:11][O:6][CH2:1][C:2]1[CH:3]=[CH:4][C:16]([CH:17]=[CH2:18])=[CH:15][CH:14]=1Komponenten
Versuchsvorschrift
Butanediol (40 ml; 40.68 g; 0.452 mol) was stirred in a 100 ml round bottomed flask, and treated portionwise with potassium butoxide (17.60 g; 0.144 mol). The initial reaction was exothermic. The reaction mixture was stirred for 1.5 hours at room temperature. The resulting cloudy solution was then treated with chloromethyl styrene (20.00 g; 0.131 mol). The styrene formed an upper, pale green layer, (the colouration being due to the presence of inhibitor), whose color darkened considerably on the addition of 18-crown-6 (0.49 g; 1.86×10-1 mole). The flask was stoppered, protected from light, and stirred for 28 hours at room temperature. The mixture was then poured into water (120 ml) and extracted with dichloromethane (4×50 ml). The combined organic extracts were dried (MgSO4) and evaporated to give viscous yellow oil (932.7 g). This oil was distilled from a small amount of CuCl to give a product showing some impurities on TLC. The oil was then chromatographed on silica gel, initially eluting with dichloromethane/petrol (1:1) to remove the impurities. The product was then eluted off the column with ethyl acetate/petrol (1:1). Evaporation of the solvent gave a colourless oil, which was distilled to give the desired styrylbutyl alcohol as a colourless oil b.pt. 150°-152° /0.4 mbar. Yield 18.70 g; 69.2%.
Aufarbeitung
- customThe initial reaction
Quellen und Nachweise
- ORD-Eintrag
- ord-3156c37e69c345eabe66b8082a62d4b0
- Quelldatensatz
- uspto-grants-1998_01
- Patentnummer
- US05712326
Verknüpfte Notizen
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