Benzaldehyde → 5,10,15,20-Tetraphenyl-21,22-dihydroporphyrin

HRID 1285180

Reaction equation

HRID 1285180 reaction equation
[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:9]1[CH:13]=[CH:12][CH:11]=[CH:10]1>C(O)(=O)CC>[CH:5]1[CH:6]=[CH:7][C:2]([C:1]2[C:13]3=[N:9][C:10]([CH:11]=[CH:12]3)=[C:1]([C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[C:10]3=[N:9][C:13]([CH:12]=[CH:11]3)=[C:1]([C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[C:10]3[NH:9][C:13](=[CH:12][CH:11]=3)[C:1]([C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[C:10]3[NH:9][C:13]=2[CH:12]=[CH:11]3)=[CH:3][CH:4]=1

Participants

4

Reactant 2

HCID 240BenzaldehydeHCID 8027Pyrrole

Product 1

HCID 701865,10,15,20-Tetraphenyl-21,22-dihydroporphyrinYield 20%

Reagents, catalysts & solvents 1

HCID 1032Propionic AcidSolvent

Procedure

In a 4-liter flask equipped with a cooling tube, 80 ml (84.8 g) of benzaldehyde, 56 ml (53.6 g) of pyrrol, and 3 liters of propionic acid were placed and reacted for 30 minutes under reflux. Then, the flask was allowed to stand for one day. After filtering the reaction mixture, recrystallization from a mixed solvent of methanol and chloroform (1:1 by weight) was carried out for purification. Thus, α,β,γ,δ-tetraphenylporphine was obtained in 20% yield.

Workup

  1. customIn a 4-liter flask equipped with a cooling tube
  2. customreacted for 30 minutes
  3. temperatureunder reflux
  4. filtrationAfter filtering
  5. customthe reaction mixture, recrystallization from a mixed solvent of methanol and chloroform (1:1 by weight)
  6. customwas carried out for purification

Sources & evidence

ORD record
ord-859db4873ea24be38b035e34961c91aa
Source dataset
uspto-grants-1986_01
Patent number
US04565845

Linked notes

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