Potassium Carbonate → HCID 53623237, compound

3-Ethoxy-4-methoxybenzaldehyde (4.5 g, 25 mmol), K2CO3 (5.2 g, 37.5 mmol), and diethylcyanomethyl phosphonate (4.2 mL, 26.3 mmol) were combined in ethanol (75 mL). The mixture was stirred at reflux for 1.5 h. After all benzaldehyde had been consumed, the reaction mixture was concentrated to about 15 mL, and diluted with CH2Cl2 (150 mL) and H2O (150 mL). The mixture was shaken in a separatory funnel and the layers separated. The organic layer was dried with Na2SO4, filtered and concentrated. The crude product was then titurated from ether to afford >99% of the (E)-3-(3-ethoxy-4-methoxyphenyl)-acrylonitrile 3.03 g as a light tan powder, 60%: 1H NMR (400 M Hz, CDCl3) δ 7.32 (d, 1H, J=16.4 Hz), 7.03 (dd, 1H, J=8.4, 2.0 Hz), 6.94 (d, 1H, J=2.0 Hz), 6.87 (d, 1H, J=8.4 Hz), 6.51 (d, 1H, J=16.8 Hz), 4.11 (q, 2H, J=6.8 Hz), 3.91 (s, 3H), 1.49 (t, 3H, J=6.8 Hz).

1. temperatureat reflux for 1.5 h
2. customAfter all benzaldehyde had been consumed
3. concentrationthe reaction mixture was concentrated to about 15 mL
4. additiondiluted with CH2Cl2 (150 mL) and H2O (150 mL)
5. stirringThe mixture was shaken in a separatory funnel
6. customthe layers separated
7. dry with materialThe organic layer was dried with Na2SO4
8. filtrationfiltered
9. concentrationconcentrated

ORD record

ord-2e7fb064bbcf4c60be39e9f4d40a8d62

Source dataset

uspto-grants-2008_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07470723B2