Reaktion #495254

Reaktionsgleichung

acryloyl chloride

2,4-bis(4-dibenzofuranyl)phenol

methylene chloride

triethylamine

→

foregoing white solid

Ausbeute 79.0%

2,4-bis(4-dibenzofuranyl)phenyl acrylate

Ausbeute 79.0%

Lösungsmittel

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeto form a transparent solution
2. 2
   workup.ADDITIONafter adding the whole
3. 3
   Sonstigeis returned to room temperature
4. 4
   workup.STIRRINGthe mixture is vigorously stirred
5. 5
   Sonstigean aqueous layer is then removed
6. 6
   Waschenthe aqueous layer is washed with methylene chloride
7. 7
   Trocknenand the mixture is dried upon application of magnesium sulfate
8. 8
   EinengenThe resulting mixture is concentrated by filtration with a filter paper
9. 9
   Sonstigeand the concentrate is separated by a silica gel column (eluate: hexane/ethyl acetate=90/10 (volume ratio))
10. 10
    Einengento concentrate a component

Vorschrift

1.89 g of the thus obtained 2,4-bis(4-dibenzofuranyl)phenol is placed in a round bottom flask; 20 mL of methylene chloride is added to form a transparent solution; after ice cooling the flask, 0.54 g of triethylamine is added; 0.48 g of acryloyl chloride is then added dropwise; after adding the whole, the temperature is returned to room temperature; and the mixture is stirred for 30 minutes. 10 mL of water is added; the mixture is vigorously stirred; an aqueous layer is then removed; the aqueous layer is washed with methylene chloride and gathered with the original methylene chloride solution; and the mixture is dried upon application of magnesium sulfate. The resulting mixture is concentrated by filtration with a filter paper; and the concentrate is separated by a silica gel column (eluate: hexane/ethyl acetate=90/10 (volume ratio)) to concentrate a component having an Rf of 0.20, thereby obtaining 1.69 g (yield: 79%) of the foregoing white solid. 1H NMR (CDCl3, 400 MHz): δ (ppm) 5.66 (dd=1.2 & 10.8 Hz, 1H), 5.98 (dd=10.8 & 17.2 Hz, 1H), 6.28 (dd=1.2 & 17.2 Hz, 1H), 7.34 to 7.38 (m, 2H), 7.41 to 7.46 (m, 4H), 7.51 to 7.61 (m, 4H), 7.66 to 7.68 (m, 1H), 7.95 to 7.98 (m, 4H), 7.99 to 8.00 (m, 1H), 8.05 to 8.06 (m, 1H)

Quelle