Ceric ammonium nitrate → HCID 22054145, compound

HRID 1830442Notes

Reaction equation

HRID 1830442 reaction equation
C[O:2][C:3]1[C:21]([CH3:22])=[C:20]([CH3:23])[C:19]([O:24]C)=[C:18]([CH3:26])[C:4]=1[CH2:5][C:6]1[CH:7]=[CH:8][C:9]([O:15][CH2:16][CH3:17])=[C:10]([CH:14]=1)[C:11]([OH:13])=[O:12].[O:27]=[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>[CH3:26][C:18]1[C:19](=[O:24])[C:20]([CH3:23])=[C:21]([CH3:22])[C:3](=[O:2])[C:4]=1[CH2:5][C:6]1[CH:7]=[CH:8][C:9]([O:15][C:16](=[O:27])[CH3:17])=[C:10]([CH:14]=1)[C:11]([OH:13])=[O:12]

Participants

5

Reactant 2

HCID 180504Ceric ammonium nitrateHCID 87941051HCID 87941051, compound

Product 1

HCID 22054145HCID 22054145, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent

Procedure

5-(2,5-Dimethoxy-3,4,6-trimethylbenzyl)-2-etoxybenzoic acid (1.25 g, 2.56 mmol) was dissolved in a mixed solution of acetonitrile (30 ml) and water (10 ml) and after adding thereto CAN (3.50 g, 6.39 mmol), the solution was stirred at room temperature for 1 hour. The reaction solution was diluted with water and then extracted with ether. The extract was washed with water and then dried, and the solvent was removed by distillation. The obtained residue was purified by silica gel column chromatography (hexand:ethyl acetate=2:1) and then recrystallized from ether to obtain the titled compound (0.800 g, 1.74 mmol, 68%).

Workup

  1. additionafter adding
  2. extractionextracted with ether
  3. washThe extract was washed with water
  4. customdried
  5. customthe solvent was removed by distillation
  6. customThe obtained residue was purified by silica gel column chromatography (hexand:ethyl acetate=2:1)
  7. customrecrystallized from ether

Sources & evidence

ORD record
ord-7896ae6e40994bd0808e79db002d68ab
Source dataset
uspto-grants-2006_06
Patent number
US07064124B2

Reaction notes

Loading…