Ceric ammonium nitrate → 5-(5,6-Dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-(2-methoxyphenyl)benzoic acid

HRID 1245203Notes

Reaction equation

HRID 1245203 reaction equation
C[O:2][C:3]1[C:4]([CH3:33])=[C:5]([C:24]([O:31]C)=[C:25]([O:29][CH3:30])[C:26]=1[O:27][CH3:28])[CH2:6][C:7]1[CH:8]=[CH:9][C:10]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[O:22][CH3:23])=[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>[CH3:28][O:27][C:26]1[C:3](=[O:2])[C:4]([CH3:33])=[C:5]([CH2:6][C:7]2[CH:8]=[CH:9][C:10]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[O:22][CH3:23])=[C:11]([CH:15]=2)[C:12]([OH:14])=[O:13])[C:24](=[O:31])[C:25]=1[O:29][CH3:30]

Participants

5

Reactant 2

HCID 180504Ceric ammonium nitrateHCID 121472865-(3,4,5,6-Tetramethoxy-2-methylbenzyl)-2-(2-methoxyphenyl)benzoic acid

Product 1

HCID 219191365-(5,6-Dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-(2-methoxyphenyl)benzoic acidYield 76%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent

Procedure

5-(3,4,5,6-Tetramethoxy-2-methylbenzyl)-2-(2-methoxyphenyl)benzoic acid (1.21 g, 2.6769 mmol) was dissolved in a mixed solvent of acetonitrile (30 ml) and water (10 ml), then CAN (3.60 g, 6.6914 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 (859 mg, 2.0355 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-5806cd63b952455aa51c4f768342bace
Source dataset
uspto-grants-2006_10
Patent number
US07122543B2

Reaction notes

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