Water → 1-(4-(Methoxymethyl)phenyl)ethan-1-one

HRID 1771286

Reaktionsgleichung

Reaktionsgleichung von HRID 1771286
C[O:2][CH2:3][C:4]1C=CC(C#N)=CC=1.C[Mg]I.[C:15]1([CH3:21])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[CH3:22][OH:23].O>C1COCC1.C(OCC)C>[CH3:22][O:23][CH2:21][C:15]1[CH:20]=[CH:19][C:18]([C:3](=[O:2])[CH3:4])=[CH:17][CH:16]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 132851414-(Methoxymethyl)benzonitrileHCID 21867641Toluene methanolHCID 178418373HCID 178418373, Verbindung

Produkt 1

HCID 895901-(4-(Methoxymethyl)phenyl)ethan-1-oneAusbeute 55 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21868444Ether tetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-10 °C

Versuchsvorschrift

4-(Methoxymethyl)benzonitrile (6.0 g, 40.82 mmol) was dissolved in THF/diethyl ether (1:1, 60 mL) and the resulting solution was cooled to −10° C. 3 M solution of methyl magnesium iodide (13.57 g, 81.63 mmol) was added and the resulting mixture was stirred at this temperature for 5 hours. After completion of the reaction (TLC; toluene/methanol, 97:3), the mixture was poured into acidified water (50 mL; pH 3-4) and extracted with ethyl acetate (3×50 mL). The separated organic layers were combined, dried over Na2SO4 and concentrated in vacuo. The crude compound was purified by gradient flash chromatography, eluting with 8% ethyl acetate in hexane to afford the target compound (3.7 g, 55%).

Aufarbeitung

  1. extractionextracted with ethyl acetate (3×50 mL)
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe crude compound was purified by gradient flash chromatography
  5. washeluting with 8% ethyl acetate in hexane

Quellen und Nachweise

ORD-Eintrag
ord-cf87f59390524dae80024d98d8c31136
Quelldatensatz
uspto-grants-2016_02
Patentnummer
US09249130B2

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