Reaktion #67485

Reaktionsgleichung

4-nitrophthalonitrile

pentyl 4-hydroxybenzoate

potassium carbonate

→

4-(4-pentyloxycarbonylphenoxy)phthalonitrile

Ausbeute 85.0%

Lösungsmittel

ethyl acetate

water

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturAfter cooling to room temperature
2. 2
   SonstigeThe organic layer was separated
3. 3
   Extraktionthe aqueous phase was extracted with ethyl acetate (2×50 mL)
4. 4
   WaschenThe combined organic layers were washed with a saturated solution of NaHCO3 (40 mL), brine (40 mL)
5. 5
   Trocknendried over anhydrous sodium sulfate
6. 6
   SonstigeThe solvents were removed in vacuo
7. 7
   Sonstigethe crude product was purified by column chromatography on silica gel using a dichloromethane/acetonitrile mixture (20:1) as an eluent
8. 8
   Sonstigeto give the product in 85% yield

Vorschrift

A mixture of 4-nitrophthalonitrile (1.00 g, 7 mmol), pentyl 4-hydroxybenzoate (1.45 g, 7 mmol) and dried potassium carbonate (6.38 g, 46.2 mmol) in anhydrous DMF (50 mL) was stirred overnight at 85° C. under argon. After cooling to room temperature, the mixture was diluted with ethyl acetate (60 mL) and water (40 mL). The organic layer was separated, and the aqueous phase was extracted with ethyl acetate (2×50 mL). The combined organic layers were washed with a saturated solution of NaHCO3 (40 mL), brine (40 mL) and dried over anhydrous sodium sulfate. The solvents were removed in vacuo, and the crude product was purified by column chromatography on silica gel using a dichloromethane/acetonitrile mixture (20:1) as an eluent to give the product in 85% yield. [1H NMR (δ, ppm, CDCl3): 8.15 (d, 2H, J=8.7 Hz), 7.77 (d, 1H, J=8.7 Hz), 7.35 (d, 1H, J=2.3 Hz), 7.30 (d, 1H, J=8.7 Hz), 7.12 (d, 2H, J=8.7 Hz), 4.34 (2H, t, OCH2, J=6.7 Hz), 1.79 (m, 2H, CH2), 1.42 (m, 4H, CH2CH2), 0.94 (t, 3H, J=7 Hz, CH3).]

Quelle