Ammonium cerium (IV) nitrate → 1,4-Naphthalenedione, 2-(1-hydroxypentyl)-5,8-dimethoxy-

HRID 1939738Notes

Reaction equation

HRID 1939738 reaction equation
[OH:1][CH:2]([C:8]1[CH:17]=[C:16]([O:18]C)[C:15]2[C:10](=[C:11]([O:22][CH3:23])[CH:12]=[CH:13][C:14]=2[O:20][CH3:21])[C:9]=1[O:24]C)[CH2:3][CH2:4][CH2:5][CH2:6]C.[N+]([O-])([O-])=O.[NH4+].[Ce+4].[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.[N+]([O-])([O-])=O>C(#N)C.O>[OH:1][CH:2]([C:8]1[C:9](=[O:24])[C:10]2[C:15]([C:16](=[O:18])[CH:17]=1)=[C:14]([O:20][CH3:21])[CH:13]=[CH:12][C:11]=2[O:22][CH3:23])[CH2:3][CH2:4][CH2:5][CH3:6]

Participants

5

Reactant 2

HCID 9869224Ammonium cerium (IV) nitrateHCID 21468091HCID 21468091, compound

Product 1

HCID 105186011,4-Naphthalenedione, 2-(1-hydroxypentyl)-5,8-dimethoxy-Yield 48%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent

Procedure

3.6 g (10.3 mmole) of 2-(1-hydroxyhexyl)-1,4,5,8-tetramethoxynaphthalene was dissolved in 50 ml of acetonitrile and then a solution of 14.2 g (25.0 mmole) of cerium (IV) ammonium nitrate dissolved in 50 ml of distilled water was added dropwise thereto over 30 minutes through a dropping funnel in a cooling bath (0°-5° C.). The reaction mixture was stirred at normal temperature for 2 hours. After adding 100 ml of distilled water thereto, the reaction mixture was extracted twice with dichloromethane solvent, dried over anhydrous magnesium sulfate and then filtered through filter paper. The resulting filtrate was concentrated under reduced pressure to obtain a crude product. The crude product was purified by silica gel column chromatography (silica gel 4.0×15 cm) using the solvent condition which increases the amount of ethylacetate so that the n-hexane/ethylacetate ratio can vary from 5:1 to 1:3, to obtain 1.2 g of the title compound as a yellow precipitate.

Workup

  1. additionwas added dropwise
  2. extractionthe reaction mixture was extracted twice with dichloromethane solvent
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. filtrationthrough filter paper
  6. concentrationThe resulting filtrate was concentrated under reduced pressure
  7. customto obtain a crude product
  8. customThe crude product was purified by silica gel column chromatography (silica gel 4.0×15 cm)
  9. temperatureincreases the amount of ethylacetate so that the n-hexane/ethylacetate ratio

Sources & evidence

ORD record
ord-48a16014f2324ab9a81be88829277fc4
Source dataset
uspto-grants-1997_12
Patent number
US05696276

Reaction notes

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