3-Hydroxybenzaldehyde → 3-(8-(1,3-Dioxolan-2-yl)octyloxy)benzaldehyde
Reaktionsgleichung
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH:10]1[O:14][CH2:13][CH2:12][O:11]1.[OH:15][C:16]1[CH:17]=[C:18]([CH:21]=[CH:22][CH:23]=1)[CH:19]=[O:20].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O>[O:11]1[CH2:12][CH2:13][O:14][CH:10]1[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][O:15][C:16]1[CH:17]=[C:18]([CH:21]=[CH:22][CH:23]=1)[CH:19]=[O:20]Komponenten
6
Reaktionsbedingungen
- Temperatur
- 80 °C
Versuchsvorschrift
To a stirred solution of 2-(8-bromooctyl)-1,3-dioxolane (5 g, 18.85 mmol) in dimethyl formamide (100 mL) was added 3-hydroxybenzaldehyde (2.37 g, 19.42 mmol) and potassium carbonate (5.37 g, 38.83 mmol). The reaction mixture was stirred at 80° C. for 16 hours. The reaction mixture was diluted with water and extracted with ethyl acetate (×3). The combined organic extracts were washed with saturated aqueous sodium hydrogen carbonate solution and brine, dried (sodium sulfate), filtered, and concentrated under reduced pressure. The crude material was purified by silica gel column chromatography eluting with 0-100% ethyl acetate in iso-hexane to afford the title compound (4.66 g, 78%).
Aufarbeitung
- extractionextracted with ethyl acetate (×3)
- washThe combined organic extracts were washed with saturated aqueous sodium hydrogen carbonate solution and brine
- dry with materialdried (sodium sulfate)
- filtrationfiltered
- concentrationconcentrated under reduced pressure
- customThe crude material was purified by silica gel column chromatography
- washeluting with 0-100% ethyl acetate in iso-hexane
Quellen und Nachweise
- ORD-Eintrag
- ord-7ea8671f9a0a407fa9595951e2b5b456
- Quelldatensatz
- uspto-grants-2014_11
- Patentnummer
- US08877774B2
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