3-Hydroxybenzaldehyde → 5,10,15,20-Tetrakis(3-hydroxyphenyl)porphyrin

HRID 1296327Notes

Reaction equation

[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=O.[NH:10]1[CH:14]=[CH:13][CH:12]=[CH:11]1>C(O)(=O)CC>[OH:1][C:2]1[CH:3]=[C:4]([C:5]2[C:14]3[NH:10][C:11]([C:5]([C:4]4[CH:7]=[CH:8][CH:9]=[C:2]([OH:1])[CH:3]=4)=[C:11]4[N:10]=[C:14]([C:5]([C:4]5[CH:7]=[CH:8][CH:9]=[C:2]([OH:1])[CH:3]=5)=[C:11]5[NH:10][C:14](=[C:5]([C:4]6[CH:7]=[CH:8][CH:9]=[C:2]([OH:1])[CH:3]=6)[C:11]6[CH:12]=[CH:13][C:14]=2[N:10]=6)[CH:13]=[CH:12]5)[CH:13]=[CH:12]4)=[CH:12][CH:13]=3)[CH:7]=[CH:8][CH:9]=1

Participants

Conditions

Temperature: 140 °C

Procedure

3-Hydroxybenzaldehyde (0.910 g, 7.45 mmol) is dissolved in propionic acid (50 mL) and heated to 140° C. Pyrrole (0.52 mL, 7.45 mmol) is added in one portion and the mixture heated at reflux for 2 h. Stirring is continued for an additional 12 h at room temperature. Propionic acid is removed in vacuo and the residue dissolved in acetone and purified by chromatography on a column (250 g) of silica which is eluted with toluene containing a continuously increasing proportion of ethyl acetate. The product is eluted with toluene:ethyl acetate (6:1 by vol.). Solvent is removed in vacuo to afford the product as a violet solid.

Workup

temperaturethe mixture heated
temperatureat reflux for 2 h
customPropionic acid is removed in vacuo
dissolutionthe residue dissolved in acetone
custompurified by chromatography on a column (250 g) of silica which
washis eluted with toluene containing
temperaturea continuously increasing proportion of ethyl acetate
washThe product is eluted with toluene:ethyl acetate (6:1 by vol.)
customSolvent is removed in vacuo

Sources & evidence

ORD record: ord-9c44fe29e2e14f938ffe249aea065329
Source dataset: uspto-grants-2007_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07244841B2

Reaction notes

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