Water → 4-Methoxy-3-[6-(4-phenylbut-1-yloxy)hex-1-yloxy]benzaldehyde
Reaktionsgleichung
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH:5]=[O:6].C(=O)([O-])[O-].[K+].[K+].Br[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][O:25][CH2:26][CH2:27][CH2:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.O>CN(C)C=O>[CH3:11][O:10][C:9]1[CH:8]=[CH:7][C:4]([CH:5]=[O:6])=[CH:3][C:2]=1[O:1][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][O:25][CH2:26][CH2:27][CH2:28][CH2:29][C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1Komponenten
6
Reaktionsbedingungen
- Temperatur
- 80 °C
Versuchsvorschrift
To a stirred solution of 3-hydroxy-4-methoxybenzaldehyde (4.8 grams) in dimethylformamide (100 ml) at room temperature is added potassium carbonate (4.9 grams) and 1-bromo-6-(4-phenylbut-1-yloxy)hexane (10.0 grams). After stirring at 80° C. over 4 hours the reaction mixture is poured into water and extracted with ethyl acetate. The combined organics are washed with 1N sodium hydroxide and brine, dried over sodium sulfate, filtered and concentrated under reduced pressure. The resulting amber oil is filtered through a 5×10 cm pad of silica gel, eluting with a 1:3 mixture of ethyl acetate and hexane, to give 12.0 grams of a colorless oil. MS (m/z) 384.
Aufarbeitung
- extractionextracted with ethyl acetate
- washThe combined organics are washed with 1N sodium hydroxide and brine
- dry with materialdried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated under reduced pressure
- filtrationThe resulting amber oil is filtered through a 5×10 cm pad of silica gel
- washeluting with a 1:3 mixture of ethyl acetate and hexane
Quellen und Nachweise
- ORD-Eintrag
- ord-d9a5e50754914e5992451769dfb68347
- Quelldatensatz
- uspto-grants-2000_02
- Patentnummer
- US06028086
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