Pyrrole → Tetraphenylporphyrin

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Reaction Steps

The acid derivative of 5,10,15,20-tetrakis(phenyl)porphyrin was prepared according to the procedure of Longo, et al. J. Heterocyclic Chem., 6, 927 (1969). 1.50 g 4-Carboxy-benzaldehyde (0.01 mole) and 0.69 mL pyrrole (0.01 mole) were combined in 150 mL propionic acid. The mixture was refluxed for 2 to 4 hours, cooled to room temperature, and then filtered through a fine frit. The resulting solid was then extracted into methanol and filtered through a medium frit. The filtrate was placed in a round-bottom flask, and the methanol removed on a rotary evaporator, leaving a solid purple residue. The recovered solid was then dried overnight under vacuum.

Provenance & Evidence