Potassium Carbonate → Pentyl 4-(3,4-dicyanophenoxy)benzoate

Temperature

85 °C

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).]

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

ORD record

ord-55bb5dca550f4cd6ac687da0cbf92ba2

Source dataset

uspto-grants-2013_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08524891B2