Ceric ammonium nitrate → HCID 21919130, compound

HRID 1245199Notes

Reaction equation

HRID 1245199 reaction equation
C[O:2][C:3]1[C:4]([CH3:31])=[C:5]([C:22]([O:29]C)=[C:23]([O:27][CH3:28])[C:24]=1[O:25][CH3:26])[CH2:6][C:7]1[CH:8]=[CH:9][C:10]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:11]([CH:15]=1)[C:12]([OH:14])=[O:13].O=[N+]([O-])[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[Ce+4].[NH4+].[NH4+]>C(#N)C.O>[CH3:26][O:25][C:24]1[C:3](=[O:2])[C:4]([CH3:31])=[C:5]([CH2:6][C:7]2[CH:8]=[CH:9][C:10]([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)=[C:11]([CH:15]=2)[C:12]([OH:14])=[O:13])[C:22](=[O:29])[C:23]=1[O:27][CH3:28]

Participants

5

Reactant 2

HCID 180504Ceric ammonium nitrateHCID 12147281HCID 12147281, compound

Product 1

HCID 21919130HCID 21919130, compoundYield 76.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent

Procedure

5-(3,4,5,6-Tetramethoxy-2-methylbenzyl)-2-phenylbenzoic acid (340 mg, 0.7819 mmol) was dissolved in a mixed solvent of acetonitrile (30 ml) and water (10 ml), then CAN (1.10 g, 2.0072 mmol) was added thereto at room temperature and the mixture was stirred for 3 hour. The reaction solution was poured into water and extracted with ether. The extract was washed with water and dried and the solvent was evaporated therefrom. The residue was purified by silica gel column chromatography (5% methanol-methylene chloride) to give the title compound (234 mg, 0.5969 mmol, 76%).

Workup

  1. extractionextracted with ether
  2. washThe extract was washed with water
  3. customdried
  4. customthe solvent was evaporated
  5. customThe residue was purified by silica gel column chromatography (5% methanol-methylene chloride)

Sources & evidence

ORD record
ord-4f2720fe27974c7eac88768a7f574d55
Source dataset
uspto-grants-2006_10
Patent number
US07122543B2

Reaction notes

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