ChemicalBook CAS DataBase List 4-HYDROXY-4'-NITROSTILBENE

4-HYDROXY-4'-NITROSTILBENE synthesis

10synthesis methods

Product Name:4-HYDROXY-4'-NITROSTILBENE
CAS Number:19221-08-0
Molecular formula:C14H11NO3
Molecular Weight:241.24

99-99-0
321 suppliers
$5.00/5G

123-08-0 Synthesis

123-08-0
928 suppliers
$5.00/10g

19221-08-0
32 suppliers
$46.79/1g

Yield:19221-08-0 19%

Reaction Conditions:

with pyrrolidine at 70 - 75; for 38 h;

Steps:

4-(4-Nitrostyryl)phenol (2a)

The synthesis followed the methodology described in the literature [45]. 4-Nitrotoluene (1.00 g; 7.3 mmol), 4-hydroxybenzaldehyde (0.89 g; 7.3 mmol) and pyrrolidine (1.5 mL; 18.3 mmol) were mixed and the reaction was refluxed at 70-75 °C under magnetic stirring for 38 h. The crude product was separated by silica gel column chromatography using hexane/ethyl acetate (2/3 v/v), the solvent was rotary-evaporated and the solid obtained was subsequently recrystallized from ethyl acetate. The product was a light orange solid (19% yield); m.p. obtained: 204-206 °C; m.p. literature [46]: 206 °C; IR (KBr, ): 3418 (O-H), 1584, 1501, and 1437 (C=C), 1337 (N=O); ¹H NMR (DMSO-d₆, 400 MHz) δ/ppm: 9.77 (s, 1H), 8.18 (d, 2H, J = 8.0 Hz), 7.77 (d, 2H, J = 8.0 Hz), 7.50 (d, 2H, J = 8.0 Hz), 7.42 (d, 1H, J = 16.0 Hz), 7.16 (d, 1H, J = 16.0 Hz), 6.80 (d, 2H, J = 8.0 Hz).

References:

Nandi, Leandro G.;Nicoleti, Celso R.;Stock, Rafaela I.;Barboza, Tainá A.;Andreaus, Jürgen;Machado, Vanderlei G. [Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy,2015,vol. 136,# PC,p. 1600 - 1606]