Potassium Carbonate → (3-(8-(1,3-Dioxolan-2-yl)octyloxy)phenyl)(phenyl)methanone

HRID 332646

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:27]=[CH:28][CH:29]=1)[C:19]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[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]([C:19]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:20])[CH:27]=[CH:28][CH:29]=1

Komponenten

Reaktionsbedingungen

Temperatur: 80 °C

Versuchsvorschrift

2-(8-Bromooctyl)-1,3-dioxolane (3.89 g, 14.69 mmol) was added to a mixture of 3-hydroxybenzophenone (3 g, 15.13 mmol) and potassium carbonate (4.17 g, 30.21 mmol) in dimethyl formamide (50 mL). 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 bicarbonate solution, saturated aqueous ammonium chloride solution and 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 (4.73 g, 84%).

Aufarbeitung

extractionextracted with ethyl acetate (×3)
washThe combined organic extracts were washed with saturated aqueous sodium bicarbonate solution, saturated aqueous ammonium chloride solution
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-30b4a5163c4b4338a1603aac268b527c
Quelldatensatz: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08877774B2

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