Synthesis
General procedure for the synthesis of 4-(2-nitrovinyl)phenol from 4-hydroxycinnamic acid: 0.01 mol of 4-hydroxycinnamic acid, about 0.01 mol of TCICA/DMF reagent, 1 g of sodium nitrite, and 25 mL of CH2Cl2 or acetonitrile were added to a pre-cleaned round-bottomed flask with stirring and the reaction was carried out under refluxing conditions for 8 to 10 hours. The progress of the reaction was monitored by TLC. Upon completion of the reaction, the reaction mixture was washed with NaHCO3 solution and subsequently extracted with ethyl acetate. The organic layer was separated, dried with anhydrous MgSO4 and concentrated in vacuum. Finally, purification by column chromatography using ethyl acetate-hexane as eluent gave the pure product 4-(2-nitrovinyl)phenol as a yellow powder.
References
[1] Synthetic Communications, 2013, vol. 43, # 19, p. 2672 - 2677
[2] Catalysis Science and Technology, 2016, vol. 6, # 5, p. 1430 - 1434
[3] Synthesis and Reactivity in Inorganic, Metal-Organic and Nano-Metal Chemistry, 2013, vol. 43, # 8, p. 977 - 983
[4] Synthetic Communications, 2015, vol. 45, # 19, p. 2251 - 2258
