Malonic Acid → 3-(4-(3-Butyl-2-phenylnaphthalen-1-yloxy)phenyl)acrylic acid

Participants

Reaction Steps

4-[(3-Butyl-2-phenyl-1-naphthalenyl)oxy]benzaldehyde (173) (0.14 g, 0.36 mmol) was heated with malonic acid (0.12 g, 1.09 mmol) and 1 drop of piperidine in pyridine at 85° C. overnight to give the crude product as a light yellow viscous oil, which upon trituration with 1% MeOH in hexanes, yielded 81 mg (53%) of the title compound (174) as a white solid. mp 160-161° C. 1H NMR (400 MHz, CH3OH-d4): δ 0.76 (t, J=7.3 Hz, 3H), 1.15-1.30 (m, 2H), 1.40-1.55 (m, 2H), 2.60 (t, J=7.9 Hz, 2H), 6.26 (d, J=16.0 Hz, 1H), 6.56 (d, J=8.6 Hz, 2H), 7.14-7.19 (m, 2H), 7.20-7.30 (m, 3H), 7.35 (d, J=8.6 Hz, 2H), 7.37-7.42 (m, 1H), 7.46-7.56 (m, 2H), 7.70-7.77 (m, 2H), 7.91 (d, J=8.2 Hz, 1H). LCMS (APCI): m/z 423 (M+H)+, m/z 421 (M−H)−. Anal. Calc for C29H26O3.⅙H2O: C, 81.86; H, 6.24. Found: C, 81.86; H, 6.25.

Provenance & Evidence