Ceric ammonium nitrate → HCID 16661877, compound

HRID 2113994Notes

Reaction equation

HRID 2113994 reaction equation
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+].[CH2:28]([C:34]1[C:39]([CH3:40])=[C:38]([O:41]C)[C:37]([CH3:43])=[C:36]([CH3:44])[C:35]=1[O:45]C)[CH2:29][CH2:30][CH2:31][CH2:32][CH3:33]>O>[CH2:28]([C:34]1[C:35](=[O:45])[C:36]([CH3:44])=[C:37]([CH3:43])[C:38](=[O:41])[C:39]=1[CH3:40])[CH2:29][CH2:30][CH2:31][CH2:32][CH3:33]

Participants

4

Reactant 2

HCID 180504Ceric ammonium nitrate3×HCID 16661721HCID 16661721, compound

Product 1

HCID 16661877HCID 16661877, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

CAN Oxidation: A flask was charged with 1-hexyl-2,5-dimethoxy-3,4,6-trimethyl-benzene (203; 1.75 g, 7.5 mmol) and CAN (20 mL) then cooled to 0° C. A solution of CAN (8.4 g, 15.4 mmol) in water (10 mL) was added to the flask. After 1 h the reaction was complete. The reaction mixture was extracted with MTBE (3×20 mL). The combined MTBE layers were dried over MgSO4, filtered and concentrated by rotary evaporation to yield 2-hexyl-3,5,6-trimethyl-[1,4]benzoquinone (205) as a yellow-orange oil which solidified upon standing (1.64 g, 88%). 1H NMR (400 MHz; CDCl3; ppm) 2.49-2.46 (m, 2H), 2.04 (s, 3H), 2.03 (s, 6H), 1.44-1.22 (m, 8H), 0.90 (t, J=7.1 Hz, 3H).

Workup

  1. extractionThe reaction mixture was extracted with MTBE (3×20 mL)
  2. dry with materialThe combined MTBE layers were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated by rotary evaporation

Sources & evidence

ORD record
ord-46a1ff9bd99d41049f6baddb861257ae
Source dataset
uspto-grants-2008_10
Patent number
US07432305B2

Reaction notes

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