Ceric ammonium nitrate → 3-[4-(5,6-Dimethoxy-3-methyl-1,4-benzoquinon-2-ylmethyl)phenyl]acrylic acid

HRID 496333Notes

Reaction equation

HRID 496333 reaction equation
C[O:2][C:3]1[C:20]([O:21][CH3:22])=[C:19]([O:23][CH3:24])[C:18]([O:25]C)=[C:17]([CH3:27])[C:4]=1[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([CH:12]=[CH:13][C:14]([OH:16])=[O:15])=[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>[CH3:24][O:23][C:19]1[C:18](=[O:25])[C:17]([CH3:27])=[C:4]([CH2:5][C:6]2[CH:11]=[CH:10][C:9]([CH:12]=[CH:13][C:14]([OH:16])=[O:15])=[CH:8][CH:7]=2)[C:3](=[O:2])[C:20]=1[O:21][CH3:22]

Participants

5

Reactant 2

HCID 180504Ceric ammonium nitrateHCID 73183726HCID 73183726, compound

Product 1

HCID 695470173-[4-(5,6-Dimethoxy-3-methyl-1,4-benzoquinon-2-ylmethyl)phenyl]acrylic acidYield 84%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent

Procedure

The compound (589 mg, 1.58 mmol) obtained in Step 1 was dissolved in a mixture of acetonitrile (30 ml) and water (10 ml), to which was added CAN (1.38 g, 2.52 mmol) and the mixture was stirred at room temperature for 1 hour. The reaction mixture was poured into water and was extracted with ether. After the extract was washed with water and dried, the solvent was distilled off. The residue was purified by a silica gel column chromatography (5% methanol-methylene chloride) to yield the title compound (452 mg, 1.32 mmol, yield 84%).

Workup

  1. extractionwas extracted with ether
  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 (5% methanol-methylene chloride)

Sources & evidence

ORD record
ord-efd6c23a077b4196a199cb036686d72a
Source dataset
uspto-grants-2005_09
Patent number
US06943196B1

Reaction notes

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