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

HRID 496354Notes

Reaction equation

HRID 496354 reaction equation
C[O:2][C:3]1[C:18]([O:19][CH3:20])=[C:17]([O:21][CH3:22])[C:16]([O:23]C)=[C:15]([CH3:25])[C:4]=1[CH2:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([OH:12])=[O:11])=[CH:8][CH:7]=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>[CH3:22][O:21][C:17]1[C:16](=[O:23])[C:15]([CH3:25])=[C:4]([CH2:5][C:6]2[CH:14]=[CH:13][C:9]([C:10]([OH:12])=[O:11])=[CH:8][CH:7]=2)[C:3](=[O:2])[C:18]=1[O:19][CH3:20]

Participants

5

Reactant 2

HCID 180504Ceric ammonium nitrateHCID 223252774-(2,3,4,5-tetramethoxy-6-methylbenzyl)benzoic Acid

Product 1

HCID 99488164-(5,6-Dimethoxy-3-methyl-1,4-benzoquinon-2-ylmethyl)benzoic acidYield 85.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent

Procedure

The compound (116 mg, 0.34 mmol) obtained in Step 4 was dissolved in a mixture of acetonitrile (2.2 ml) and water (0.81 ml), to which was added CAN (447 mg, 0.82 mmol). The mixture was stirred at room temperature for 30 minutes. The reaction mixture was poured into water and was extracted with methylene chloride. After the extract was washed with water and dried, the solvent was distilled off. The residue was purified by a silica gel column chromatography (methylene chloride:methanol=8:1) to yield the title compound (92 mg, 0.29 mmol, yield 85%).

Workup

  1. extractionwas extracted with methylene chloride
  2. washAfter the extract was washed with water
  3. customdried
  4. distillationthe solvent was distilled off
  5. customThe residue was purified by a silica gel column chromatography (methylene chloride:methanol=8:1)

Sources & evidence

ORD record
ord-b14e74f2f8c14107910bbfa246b5df6c
Source dataset
uspto-grants-2005_09
Patent number
US06943196B1

Reaction notes

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