Ceric ammonium nitrate → HCID 22054199, compound

HRID 1830260Notes

Reaction equation

HRID 1830260 reaction equation
C[O:2][C:3]1[C:4]([CH3:33])=[C:5]([C:24]([O:31]C)=[C:25]([O:29][CH3:30])[C:26]=1[O:27][CH3:28])[CH2:6][C:7]1[C:12]([C:13]([OH:15])=[O:14])=[C:11]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:10]=[CH:9][CH:8]=1.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>[CH3:28][O:27][C:26]1[C:3](=[O:2])[C:4]([CH3:33])=[C:5]([CH2:6][C:7]2[C:12]([C:13]([OH:15])=[O:14])=[C:11]([O:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH:10]=[CH:9][CH:8]=2)[C:24](=[O:31])[C:25]=1[O:29][CH3:30]

Participants

5

Reactant 2

HCID 180504Ceric ammonium nitrateHCID 22054192HCID 22054192, compound

Product 1

HCID 22054199HCID 22054199, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent

Procedure

6-(3,4,5,6-Tetramethoxy-2-methylbenzyl)-2-benzyloxybenzoic acid (106 mg, 0.2345 mmol) was dissolved in a mixed solution of acetonitrile (6 ml) and water (2 ml) and after adding thereto CAN (321 mg, 0.5857 mmol) at room temperature, 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 residue was recrystallized from ether to obtain the titled compound (62 mg, 0.1469 mmol, 64%).

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 residue was recrystallized from ether

Sources & evidence

ORD record
ord-6d81c88ff6774a81a692e74b8417de47
Source dataset
uspto-grants-2006_06
Patent number
US07064124B2

Reaction notes

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