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

HRID 1245197Notes

Reaction equation

HRID 1245197 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:15]=[CH:14][C:10]([C:11]([OH:13])=[O:12])=[C:9]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:8]=1.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:15]=[CH:14][C:10]([C:11]([OH:13])=[O:12])=[C:9]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH:8]=2)[C:22](=[O:29])[C:23]=1[O:27][CH3:28]

Participants

5

Reactant 2

HCID 180504Ceric ammonium nitrateHCID 121472794-(3,4,5,6-Tetramethoxy-2-methylbenzyl)-2-phenylbenzoic Acid

Product 1

HCID 219191464-(5,6-Dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-phenylbenzoic acidYield 77%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent

Procedure

4-(3,4,5,6-Tetramethoxy-2-methylbenzyl)-2-phenylbenzoic acid (76 mg, 1.1800 mmol) was dissolved in a mixed solvent of acetonitrile (3 ml) and water (1 ml), then CAN (247 mg, 0.4507 mmol) was added thereto at room temperature and the mixture was stirred for 1 hour. The reaction solution was poured into water and extracted with ethyl acetate. 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 (54 mg, 0.1377 mmol, 77%).

Workup

  1. extractionextracted with ethyl acetate
  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-1cccbdb274054ec296d70cb8e18af487
Source dataset
uspto-grants-2006_10
Patent number
US07122543B2

Reaction notes

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