An improved synthesis of tetramesitylporphyrin

✍ Scribed by Richard W. Wagner; David S. Lawrence; Jonathan S. Lindsey

• Book ID: 104227710
• Publisher: Elsevier Science
• Year: 1987
• Tongue: French
• Weight: 151 KB
• Volume: 28
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)96287-7

✦ Synopsis

We report a simple two-step one-flask procedure for the synthesis of tetramesitylporphyrin in 29% yield. Pyrrole and mesitaldehyde react at room temperature to form tetramesitylporphyrinogen. The addition of an oxidant yields the porphyrin. Macrocycle formation and oxidative aromatization are thus performed separately. The reaction at higher temperature results in a lower yield of porphyrin. 5. The Zn-dipyrrylmethene from 2,6-dichlorobenzaldehyde and pyrrole was isolated from refluxing collidine (171-C) in 40% yield, but the porphyrin yield was only 3.7%. See: