Ceric ammonium nitrate → HCID 18348612, compound

HRID 2268526Notes

Reaction equation

HRID 2268526 reaction equation
[C:1]([O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH:13]1[CH2:21][C:20]2[C:15](=[C:16]([O:28]C)[C:17]([O:26][CH3:27])=[C:18]([O:24][CH3:25])[C:19]=2[O:22]C)[CH2:14]1)(=[O:3])[CH3:2].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>[C:1]([O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH:13]1[CH2:21][C:20]2[C:19](=[O:22])[C:18]([O:24][CH3:25])=[C:17]([O:26][CH3:27])[C:16](=[O:28])[C:15]=2[CH2:14]1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 180504Ceric ammonium nitrateHCID 18348603HCID 18348603, compound

Product 1

HCID 18348612HCID 18348612, compoundYield 60.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent

Procedure

To a solution of 8-(4,5,6,7-tetramethoxyindan-2-yl)octyl acetate (1.25 g) in acetonitrile (13 ml) was dropwise added a solution of CAN (4.19 g) in water (13 ml) with cooling with ice. After the reaction mixture was stirred for 15 min, water was added to the reaction mixture, which was extracted with ethyl acetate. The organic layer was washed with water and saturated aqueous sodium chloride, and dried. The solvent was removed in vacuo. The residue was purified by silica gel column chromatography (hexane to hexane:ethyl acetate=10:1) and then with recrystallization from hexane-diethyl ether to yield the entitled compound (700 mg) as crystals.

Workup

  1. temperaturewith cooling with ice
  2. extractionwas extracted with ethyl acetate
  3. washThe organic layer was washed with water and saturated aqueous sodium chloride
  4. customdried
  5. customThe solvent was removed in vacuo
  6. customThe residue was purified by silica gel column chromatography (hexane to hexane:ethyl acetate=10:1)
  7. customwith recrystallization from hexane-diethyl ether

Sources & evidence

ORD record
ord-2ef13356d9944d92a960ae357de81609
Source dataset
uspto-grants-2001_12
Patent number
US06326369B1

Reaction notes

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