Water → 4-(Allyloxy)benzonitrile

HRID 603381Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 603381
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.[CH2:10](Br)[CH:11]=[CH2:12].C([O-])([O-])=O.[Cs+].[Cs+].O>CN(C=O)C>[CH2:12]([O:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1)[CH:11]=[CH2:10]

Komponenten

6

Edukt 4

HCID 962WaterHCID 7841Allyl bromideHCID 10796Cesium carbonateHCID 130194-Cyanophenol

Produkt 1

HCID 2579494-(Allyloxy)benzonitrileAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

4-Hydroxybenzonitrile (30.0 g, 252 mmol), allyl bromide (39.6 g, 327 mmol), and Cs2CO3 (98.5 g, 302 mmol) were dissolved in DMF (900 mL), and water (1 mL) was added. After stirring for 12 h at rt, the reaction mixture was concentrated under reduced pressure, water was added, and the mixture was extracted with EtOAc (2×). The combined organic layers were washed with water and brine. The organic layer was dried over Na2SO4, filtered, and concentrated under reduced pressure yielding 40 g (100%) of the title compound as a white crystalline solid. 1H NMR (400 MHz, CDCl3): δ 4.60 (d, 2H), 5.34 (d, 1H), 5.43 (d, 1H), 6.03 (m, 1H), 6.96 (d, 2H), 7.58 (d, 2H).

Aufarbeitung

  1. concentrationthe reaction mixture was concentrated under reduced pressure, water
  2. additionwas added
  3. extractionthe mixture was extracted with EtOAc (2×)
  4. washThe combined organic layers were washed with water and brine
  5. dry with materialThe organic layer was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-1b8a9898d51542c2a06f985cce964aa3
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07906653B2

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