Benzaldehyde → HCID 135446084, compound

HRID 65544Notes

Reaction equation

HRID 65544 reaction equation
[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:9]([C:12]1[CH:19]=[CH:18][C:15]([CH:16]=O)=[CH:14][CH:13]=1)([OH:11])=[O:10].[NH:20]1[CH:24]=[CH:23][CH:22]=[CH:21]1>C(O)(=O)CC>[C:2]1([C:1]2[C:21]3[CH:22]=[CH:23][C:24]([N:20]=3)=[C:16]([C:15]3[CH:18]=[CH:19][C:12]([C:9]([OH:11])=[O:10])=[CH:13][CH:14]=3)[C:24]3[NH:20][C:21]([C:1]([C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)=[C:24]4[N:20]=[C:21]([C:1]([C:2]5[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=5)=[C:24]5[NH:20][C:21]=2[CH:22]=[CH:23]5)[CH:22]=[CH:23]4)=[CH:22][CH:23]=3)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 8027PyrroleHCID 120884-Formylbenzoic acid

Product 1

HCID 135446084HCID 135446084, compound

Reagents, catalysts & solvents 1

HCID 1032Propionic AcidSolvent

Procedure

15.2 ml of benzaldehyde and 7.51 g of 4-carboxybenzaldehyde are dissolved in 746 ml of boiling propionic acid, treated dropwise with 13.9 ml of pyrrole, the mixture obtained is subsequently heated under reflux for about 30 minutes and then left to cool to room temperature. The porphine derivative is precipitated by the addition of 0.5 l of water. The filtered-off crude product is pre-purified by two-fold column chromatography on 1.2 kg of silica gel, in each case the elution being carried out with the following solvents in sequence: chloroform/cyclohexane (1:1), chloroform/ethyl acetate (3:2) and (1:1), ethyl acetate and ethyl acetate which contains 2% methanol. For the further purification, the product is suspended in a small amount of methanol and filtered off. This procedure is repeated until the filtrate is only faintly coloured. The thus-obtained product is then chromatographed on a silica gel column using chloroform, chloroform/ethyl acetate (1:1) and ethyl acetate as the elution agent. There are obtained 1.7 g of 4-(10,15,20-triphenyl-21H,23H-porphin- 5-yl)benzoic acid as violet crystals.

Workup

  1. customthe mixture obtained
  2. temperatureis subsequently heated
  3. temperatureunder reflux for about 30 minutes
  4. waitleft
  5. customThe porphine derivative is precipitated by the addition of 0.5 l of water
  6. customThe filtered-off crude product is pre-purified by two-fold column chromatography on 1.2 kg of silica gel, in each case
  7. washthe elution
  8. customFor the further purification
  9. filtrationfiltered off
  10. customThe thus-obtained product is then chromatographed on a silica gel column

Sources & evidence

ORD record
ord-431b0cdb38e74b3ca50046a77ca95cf3
Source dataset
uspto-grants-1986_09
Patent number
US04614723

Reaction notes

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