2-Propenoic acid, 3-(4-nitrophenyl)-, (2Z)- synthesis
- Product Name:2-Propenoic acid, 3-(4-nitrophenyl)-, (2Z)-
- CAS Number:14290-91-6
- Molecular formula:C9H7NO4
- Molecular Weight:193.16
51507-21-2
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Yield:14290-91-6 76%
Reaction Conditions:
with water;sodium hydroxide in ethanol at 20; for 4 h;
Steps:
4.2.33. (Z)-3-(4-Nitrophenyl)acrylic acid (cis-35)
General procedure: 0.52 M NaOH (10 mL) was added to a solution of cis-115 (1.50 g,9.26 mmol) in EtOH (6.0 mL) at room temperature. The mixture was stirred for 4 h, diluted with H2O (10 mL), and the acidity of the solution was adjusted with 1 M HCl to pH 1.0. The mixture was extracted with EtOAc (3 x 20 mL), washed with brine(20 mL), dried (MgSO4), and filtered.; Hydrolysis of cis-147 was performed using the procedure describedabove to afford cis-35 (76%) as yellow needles: mp 146-147 C (toluene); 1H-NMR (CDCl3, 400 MHz) d: 6.15 (d, J = 12.8 Hz, 1H, CH-CO2-), 7.15 (d, J = 12.8 Hz, 1H, Ar-CH), 7.66,8.21 (d, J = 8.8 Hz, each 2H, Ar-H); 13C-NMR (CDCl3, 100 MHz)d:122.0 (d,CH-CO2-), 123.3 (d, Ar), 130.3 (d, Ar), 140.9 (s, Ar),143.4 (d, Ar-CH), 147.8 (s, Ar), 177.8 (s, CO); IR (KBr)1705 cm1; ESI-MS m/z 192 (M+H); Anal. calcd for C9H7NO4: C,55.96; H, 3.65; N, 7.25. found: C, 56.02; H, 3.68; N, 7.23.
References:
Nishikawa, Keisuke;Fukuda, Hiroshi;Abe, Masato;Nakanishi, Kazunari;Taniguchi, Tomoya;Nomura, Takashi;Yamaguchi, Chihiro;Hiradate, Syuntaro;Fujii, Yoshiharu;Okuda, Katsuhiro;Shindo, Mitsuru [Phytochemistry,2013,vol. 96,p. 132 - 147]
555-16-8
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882-06-4
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