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

HRID 366912Notes

Reaction equation

HRID 366912 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-e7d8a8339d6240a5b029b4cb2a404e68
Source dataset
uspto-grants-2000_10
Patent number
US06130340

Reaction notes

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