Water → 5,10,15-tris-(4-Hydroxy-phenyl)-20-(4-tridecyloxy-phenyl)-porphyrin

HRID 1012684Notes

Reaction equation

HRID 1012684 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]3[NH:13][C:12]([C:14]([C:46]4[CH:51]=[CH:50][C:49]([OH:52])=[CH:48][CH:47]=4)=[C:15]4[N:45]=[C:18]([C:19]([C:38]5[CH:43]=[CH:42][C:41]([OH:44])=[CH:40][CH:39]=5)=[C:20]5[NH:37][C:23](=[C:24]([C:30]6[CH:35]=[CH:34][C:33]([OH:36])=[CH:32][CH:31]=6)[C:25]6[CH:26]=[CH:27][C:28]=2[N:29]=6)[CH:22]=[CH:21]5)[CH:17]=[CH:16]4)=[CH:11][CH:10]=3)=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][CH2:65][CH2:66][CH2:67][CH2:68][CH2:69][CH2:70][CH2:71][CH3:72].O>CN(C=O)C>[OH:52][C:49]1[CH:48]=[CH:47][C:46]([C:14]2[C:12]3[NH:13][C:9]([C:8]([C:5]4[CH:6]=[CH:7][C:2]([O:1][CH2:72][CH2:71][CH2:70][CH2:69][CH2:68][CH2:67][CH2:66][CH2:65][CH2:64][CH2:63][CH2:62][CH2:61][CH3:60])=[CH:3][CH:4]=4)=[C:28]4[N:29]=[C:25]([C:24]([C:30]5[CH:31]=[CH:32][C:33]([OH:36])=[CH:34][CH:35]=5)=[C:23]5[NH:37][C:20](=[C:19]([C:38]6[CH:43]=[CH:42][C:41]([OH:44])=[CH:40][CH:39]=6)[C:18]6[CH:17]=[CH:16][C:15]=2[N:45]=6)[CH:21]=[CH:22]5)[CH:26]=[CH:27]4)=[CH:10][CH:11]=3)=[CH:51][CH:50]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 130001-BromotridecaneHCID 1354380305,10,15,20-Tetrakis(4-hydroxyphenyl)porphyrin

Product 1

HCID 1360491725,10,15-tris-(4-Hydroxy-phenyl)-20-(4-tridecyloxy-phenyl)-porphyrin

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

5,10,15,20-tetrakis-(4-Hydroxy-phenyl)-porphyrin (400 mg, 0.59 mmol) is dissolved and K2CO3 (1.0 g, 7.1 mmol) is suspended in DMF (75 mL). To the vigorously stirred reaction mixture a solution of 1-bromotridecane (0.1 mL, 0.45 mmol) in DMF (10 mL) is added dropwise at 50° C. during 30 mins and the mixture is then heated for 1.5 h. The reaction mixture is cooled to room temperature and poured into water (150 mL). The porphyrins are extracted with ethyl acetate (100 mL) and the extract washed with brine (3×50 mL) and dried (Na2SO4). After evaporation of solvent, the residue is dissolved in toluene:ethanol (1:1, by vol., ca. 10 mL) and purified by chromatography using a column (200 g) of silica gel (Merck 60) with toluene as the eluent. After the elution of the first three compounds, the eluent is changed to toluene:ethyl acetate (2:1, by vol.). The fifth compound eluted is collected and dried under high vacuum to yield product as a violet solid.

Workup

  1. additionis added dropwise at 50° C. during 30 mins
  2. temperaturethe mixture is then heated for 1.5 h
  3. extractionThe porphyrins are extracted with ethyl acetate (100 mL)
  4. washthe extract washed with brine (3×50 mL)
  5. dry with materialdried (Na2SO4)
  6. customAfter evaporation of solvent
  7. dissolutionthe residue is dissolved in toluene:ethanol (1:1, by vol., ca. 10 mL)
  8. custompurified by chromatography
  9. washAfter the elution of the first three compounds
  10. washThe fifth compound eluted
  11. customis collected
  12. customdried under high vacuum
  13. customto yield product as a violet solid

Sources & evidence

ORD record
ord-b96eaeaa0d3d459a93256933630ce85f
Source dataset
uspto-grants-2011_07
Patent number
US07977474B2

Reaction notes

Loading…