Salicylaldehyde → 5,10,15,20-tetra(2-hydroxyphenyl)porphyrin

HRID 1377965Notes

Reaction equation

HRID 1377965 reaction equation
[NH:1]1[CH:5]=[CH:4][CH:3]=[CH:2]1.[CH:6](=O)[C:7]1[C:8](=[CH:10][CH:11]=[CH:12][CH:13]=1)[OH:9]>C(O)(=O)CC>[OH:9][C:8]1[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=1[C:6]1[C:5]2[NH:1][C:2]([C:6]([C:7]3[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=3[OH:9])=[C:2]3[N:1]=[C:5]([C:6]([C:7]4[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=4[OH:9])=[C:2]4[NH:1][C:5](=[C:6]([C:7]5[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=5[OH:9])[C:2]5[CH:3]=[CH:4][C:5]=1[N:1]=5)[CH:4]=[CH:3]4)[CH:4]=[CH:3]3)=[CH:3][CH:4]=2

Participants

4

Reactant 2

HCID 6998SalicylaldehydeHCID 8027Pyrrole

Product 1

HCID 1354748445,10,15,20-tetra(2-hydroxyphenyl)porphyrin

Reagents, catalysts & solvents 1

HCID 1032Propionic AcidSolvent

Procedure

Pyrrole (1.0 equivalents) and salicylaldehyde (1.2 equivalents) are dissolved in propionic acid (1 liter/20 ml pyrrole) and the solution is refluxed for 30 minutes. The reaction mixture is allowed to cool to room temperature and stand for one day. The mixture is filtered and the product is recrystallized to yield 5,10,15,20-tetrakis(2'-hydroxyphenyl)porphyrin.

Workup

  1. temperaturethe solution is refluxed for 30 minutes
  2. filtrationThe mixture is filtered
  3. customthe product is recrystallized

Sources & evidence

ORD record
ord-add7077e10524816906784408e256b3b
Source dataset
uspto-grants-1997_09
Patent number
US05665890

Reaction notes

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