Benzaldehyde → Benzaldehyde-O-(2-carboxyphenyl)oxime

Participants

Reaction Steps

70% HClO4 (14.0 μL, 0.163 mmol), benzaldehyde (18.0 mL, 0.177 mmol), and 20 (39.0 mg, 0.175 mmol) were subjected to the representative coupling procedure as outlined above (method 3), yielding 2a as a white solid (26.1 mg, 62%). 1H-NMR (500 MHz, d6-Acetone) δ 7.15 (dt, J=0.9, 7.8 Hz, 1H), 7.48-7.55 (m, 3H), 7.59 (dt, J=1.8, 7.8 Hz, 1H), 7.71 (d, J=8.2 Hz, 1H), 7.83-7.89 (m, 3H), 8.66 (s, 1H), 10.8-11.5 (broad s, 1H); 13C-NMR (125 MHz, d6-DMSO) δ 115.7, 119.7, 122.1, 127.8, 129.0, 130.8, 130.9, 131.1, 133.1, 153.4, 157.7, 166.8; MALDI-FTMS (DHB) 242.0811 m/z [MH]+, C14H12NO3 requires 242.0812. RP-HPLC: >99% pure.

Provenance & Evidence