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

HRID 496349Notes

Reaction equation

HRID 496349 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 100.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent

Procedure

The compound (1.98 g, 5.75 mmol) obtained in Step 2 was dissolved in a mixture of acetonitrile (40 ml) and water (15 ml), to which was added CAN (7.90 g, 14.5 mmol) and the mixture was stirred at room temperature for 40 minutes. The reaction mixture was poured into water and was extracted with ethyl acetate. After the extract was washed with water and dried, the solvent was distilled off. Ether was added to the residue and the resulting precipitate was filtered to yield the title compound (1.82 g, 5.76 mmol, yield 99%).

Workup

  1. extractionwas extracted with ethyl acetate
  2. washAfter the extract was washed with water
  3. customdried
  4. distillationthe solvent was distilled off
  5. additionEther was added to the residue
  6. filtrationthe resulting precipitate was filtered

Sources & evidence

ORD record
ord-a6dc0d53946e49e0957309d832a1732f
Source dataset
uspto-grants-2005_09
Patent number
US06943196B1

Reaction notes

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