Ceric ammonium nitrate → HCID 16034847, compound

HRID 2113995Notes

Reaction equation

HRID 2113995 reaction equation
[CH2:1]([C:9]1[C:14]([CH3:15])=[C:13]([O:16]C)[C:12]([CH3:18])=[C:11]([CH3:19])[C:10]=1[O:20]C)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].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+]>O>[CH2:1]([C:9]1[C:10](=[O:20])[C:11]([CH3:19])=[C:12]([CH3:18])[C:13](=[O:16])[C:14]=1[CH3:15])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

4

Reactant 2

HCID 180504Ceric ammonium nitrate2×HCID 16661876HCID 16661876, compound

Product 1

HCID 16034847HCID 16034847, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

A flask was charged with 1-octyl-2,5-dimethoxy-3,4,6-trimethyl-benzene (204; 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 was diluted with water (50 mL) and the yellow precipitate was filtered and washed with water (20 mL). The fine yellow needles were dried under high vacuum to give pure 2-octyl-3,5,6-trimethyl-[1,4]benzoquinone (206; 1.69 g, 86%). 1H NMR (400 MHz; CDCl3; ppm): 2.49-2.45 (m, 2H), 2.04 (s, 3H), 2.03 (s, 6H), 1.45-1.19 (m, 12H), 0.89 (t,J=6.2 Hz, 3H).

Workup

  1. filtrationthe yellow precipitate was filtered
  2. washwashed with water (20 mL)
  3. customThe fine yellow needles were dried under high vacuum

Sources & evidence

ORD record
ord-d8701c84529d40379455b29ab1f90ddb
Source dataset
uspto-grants-2008_10
Patent number
US07432305B2

Reaction notes

Loading…