Water → HCID 80741150, compound

Participants

Reaction Steps

To a solution of 2-(2-(but-3-en-1-yloxy)phenyl)acetonitrile (1.0 g, 5.34 mmol, 1 equiv) in EtOH (27 mL) was added 10 N NaOH (27 mL). The reaction was heated at reflux for 18 h. Upon cooling to ambient temperature, the reaction was diluted with water and washed with ether. The aqueous layer was acidified with concentrated HCl and extracted with DCM (×3). The combined DCM extracts were dried (Na2SO4) and concentrated in vacuo to provide the product (0.98 g, 89%) as a viscous pale yellow oil. 1H NMR (400 MHz, CDCl3) δ 11.15-9.85 (m, 1H), 7.30-7.25 (m, 1H), 7.21 (dd, J=7.3, 1.5 Hz, 1H), 6.97-6.91 (m, 1H), 6.89 (d, J=8.3 Hz, 1H), 5.98-5.82 (m, 1H), 5.21-5.14 (m, 1H), 5.10 (dd, J=10.3, 1.5 Hz, 1H), 4.06 (t, J=6.5 Hz, 2H), 3.68 (s, 2H), 2.55 (q, J=6.6 Hz, 2H).

Provenance & Evidence