12093-10-6, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. Ferrocenecarboxaldehyde, cas is 12093-10-6,the iron-catalyst compound, it is a common compound, a new synthetic route is introduced below.
General procedure: In a typical procedure, 1.39 mmol of 2?-hydroxyacetophenone (for 1 and 3) or 2?-hydroxy-4?-methoxyacetophenone (for 2 and 4) were dissolved in 40 ml of methanol. To this solution, 4 equivalent of potassium hydroxide were added and stirred for 15 min at room temperature. Then, 1.40 mmol of the appropriate ferrocenecarboxaldehyde derivative, (i.e. 1-ferrocenecarboxaldehyde for 1 and 2 or 1,1-ferrocenedicarboxaldehyde for 3 and 4) were added. The mixture was stirred during three days at room temperature. Then, methanol was evaporated in vacuum (rotary evaporator) and the crude reaction mixture was submitted to column chromatography (silica gel 60, Ethyl acetate: Hexane = 3:10 v/v). (E)-3-Ferrocenyl-1-(2-hydroxyphenyl)-prop-2-en-1-one, (1). Yield 65% (605 mg), mp. 157-159.4 C. IR (KBr) cm-1: 3456 (OH), 3105 (C-H), 3086 (C-H), 1630 (C=O). 1H NMR (CDCl3, 400 MHz): delta 4.22 (5H, s, C5H5), 4.56 (2H, s, H-beta-C5H4), 4.65 (2H, s, H-alpha -C5H4), 6.95 (1H, t, J = 7.2 Hz, Harom), 7.26 (1H, d, J = 15 Hz, =CH), 7.45 (1H, t, J = 7.2 Hz, Harom), 7.88 (1H, d, J = 9.1 Hz, Harom), 7.92 (1H, d, J = 15 Hz, =CH), 13.08 (1H, s, OH). 13C NMR (CDCl3, 400 MHz): delta: 31.34, 69.51, 69.71, 70.36, 72.27, 117.15, 119.00, 119.10, 129.79, 136.30, 148.36, 164.03, 193.17. Uv-vis: 528 nm (704.5 cm-1M-1), 340 nm (8400 cm-1M-1). Analysis calculated for C19H16O2Fe: C, 68.70; H, 4.86. Found: C, 68.22; H, 4.76.
The chemical industry reduces the impact on the environment during synthesis,12093-10-6,Ferrocenecarboxaldehyde,I believe this compound will play a more active role in future production and life.
Reference£º
Article; Trujillo, Alexander; Ocayo, Fernanda; Artigas, Vania; Santos, Juan C.; Jara-Ulloa, Paola; Kahlal, Samia; Saillard, Jean-Yves; Fuentealba, Mauricio; Escobar, Carlos A.; Tetrahedron Letters; vol. 58; 5; (2017); p. 437 – 441;,
Iron Catalysis in Organic Synthesis | Chemical Reviews
Iron Catalysis in Organic Synthesis: A Critical Assessment of What It Takes To Make This Base Metal a Multitasking Champion