[5,10,15,20-Tetrakis(4-methoxyphenyl)porphyrinato]cobalt(II)

Typical Procedure:
[5,10,15,20-Tetrakis(4-methoxyphenyl)porphyrinato]cobalt(II) (0.2 mol%), phenol (1.0 mmol), Na₂CO₃ (1.0 mmol), MeOH (4.0 mL), and H₂O (1.0 mL) are added to a 25 mL flame-dried Schlenk tube in air. The air is removed by vacuum, and O₂ (1 atm) is introduced. The Schlenk tube is then sealed, and the resulting mixture is stirred at 60 °C under an atmosphere of oxygen (1 atm). After stirring for the time indicated, the mixture is cooled to room temperature, carefully acidified with dilute aqueous HCl, diluted with AcOEt (10 mL), filtered through a plug of silica gel, and washed with AcOEt (20–30 mL). The combined organic extract is dried with anhydrous MgSO₄, filtered, and concentrated under reduced pressure. The resulting residue is purified by column chromatography on silica gel to afford the desired product.