HCID 22325304, compound → 3-[4-(5,6-Dimethoxy-3-methyl-1,4-benzoquinon-2-ylmethyl)phenyl]propionic acid

HRID 496331Notes

Reaction equation

HRID 496331 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]([CH2:12][CH2:13][C:14]([OH:16])=[O:15])=[CH:8][CH:7]=1>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]([CH2:12][CH2:13][C:14]([OH:16])=[O:15])=[CH:8][CH:7]=2)[C:3](=[O:2])[C:20]=1[O:21][CH3:22]

Participants

4

Reactant 1

HCID 22325304HCID 22325304, compound

Product 1

HCID 98410613-[4-(5,6-Dimethoxy-3-methyl-1,4-benzoquinon-2-ylmethyl)phenyl]propionic acidYield 72%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent

Procedure

The compound (1.00 g, 2.67 mmol) obtained in Step 6 was dissolved in a mixture of acetonitrile (30 ml) and water (10 ml), to which was added CAN (ceric ammonium nitrate) (2.34 g, 4.27 mmol) and the mixture was stirred at room temperature for 30 minutes. 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) and then was crystallized in ethanol/hexane to yield the title compound (662 mg, 1.92 mmol, yield 72%).

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)
  6. customwas crystallized in ethanol/hexane

Sources & evidence

ORD record
ord-ecb68165c7d445a684241e76535b66d9
Source dataset
uspto-grants-2005_09
Patent number
US06943196B1

Reaction notes

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