Acetic Acid → HCID 23579475, compound

HRID 900391Notes

Reaction equation

HRID 900391 reaction equation
[C:1]1([C:7]([C:10]2[CH:23]=[CH:22][C:21]3[C:20]([C:25]4[CH:30]=[CH:29][C:28]([CH:31]=[C:32]([C:39]5[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=5)[C:33]5[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=5)=[CH:27][CH:26]=4)(O)[C:19]4[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=4)[C:13]([C:46]4[CH:51]=[CH:50][C:49]([CH:52]=[C:53]([C:60]5[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=5)[C:54]5[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=5)=[CH:48][CH:47]=4)(O)[C:12]=3[CH:11]=2)([CH3:9])[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[I-].[K+].O.[PH2](=O)[O-].[Na+].C(O)(=O)C>O.C1(C)C=CC=CC=1>[C:1]1([C:7]([C:10]2[CH:23]=[CH:22][C:21]3[C:12](=[C:13]([C:46]4[CH:47]=[CH:48][C:49]([CH:52]=[C:53]([C:54]5[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=5)[C:60]5[CH:61]=[CH:62][CH:63]=[CH:64][CH:65]=5)=[CH:50][CH:51]=4)[C:14]4[C:19]([C:20]=3[C:25]3[CH:30]=[CH:29][C:28]([CH:31]=[C:32]([C:39]5[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=5)[C:33]5[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=5)=[CH:27][CH:26]=3)=[CH:18][CH:17]=[CH:16][CH:15]=4)[CH:11]=2)([CH3:9])[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 4875Potassium IodideHCID 68635454HCID 68635454, compoundHCID 178418950HCID 178418950, compound

Product 1

HCID 23579475HCID 23579475, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

2-(2-Phenyl-2-propyl)-9,10-bis(4-(2,2-diphenylvinyl)phenyl)-9,10-dihydro-9,10-dihydroxyanthracene (5.7 g, 6.7 mmole), potassium iodide (3.3 g, 20 mmole) and sodium phosphinate monohydrate (1.1 g, 10 mmole) were dissolved into acetic acid (50 ml), and the resultant solution was stirred at 100° C. The reaction mixture was diluted with water (50 ml) and treated by extraction with toluene (300 ml). The organic layer was washed with a saturated aqueous solution of sodium chloride (50 ml) and dried with magnesium sulfate. After the solvent was removed by distillation, the obtained product was purified in accordance with the column chromatography (silica gel; hexane+30% dichloromethane), and a light yellow solid was obtained (4.5 g; 82%). The obtained product was identified to be Compound (A21) by the measurements in accordance with 1H-NMR and FD-MS.

Workup

  1. washThe organic layer was washed with a saturated aqueous solution of sodium chloride (50 ml)
  2. dry with materialdried with magnesium sulfate
  3. customAfter the solvent was removed by distillation
  4. customthe obtained product was purified in accordance with the column chromatography (silica gel; hexane+30% dichloromethane)
  5. customa light yellow solid was obtained (4.5 g; 82%)

Sources & evidence

ORD record
ord-3253b0c442c04010bc05bbc30aff77d5
Source dataset
uspto-grants-2008_04
Patent number
US07357991B2

Reaction notes

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