Sodium Hydroxide → HCID 86752022, compound

Participants

Reaction Steps

To a solution in hot ethanol of 3,3-bis((4-(2-quinolylmethoxy)phenyl)-propenoic acid ethyl ester (560 mg, 1 mmol), prepared as in step 1, was added aqueous 1N NaOH (8 mL) and the reaction mixture was heated at reflux for 3 hours. The reaction mixture was cooled to room temperature, concentrated in vacuo, diluted with water (25 mL), and neutralized with 10% citric acid solution. The resulting precipitate was collected by filtration, washed with water, slurried in warm EtOH (20 mL), collected by filtration, and dried in vacuo to obtain 3,3-bis((4-(2-quinolyl-methoxy)phenyl)propenoic acid (265 mg): mp 127°-130° C.; 1H NMR (300 MHz, DMSO-d6)δ5.40 (s, 4H), 6.20 (s, 1H), 7.08 (m, 6H), 7.21 (d, 2H, J=9 Hz), 7.73 (m, 6H), 8.03 (m, 4H), 8.44 (t, 2H, J=9 Hz), 11.97 (bs, 1H); MS (DCI/NH3) m/e 538 (M+H)+. Anal. Calcd. for C35H26 N3O5 ×3H2O: C, 70.95; H, 5.41; N, 4.73. Found: C, 70.53; H, 5.24; N, 4.61.

Provenance & Evidence