Ceric ammonium nitrate → HCID 22054338, compound

HRID 1830259Notes

Reaction equation

HRID 1830259 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[CH:15]=[CH:14][C:10]([C:11]([OH:13])=[O:12])=[C:9]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:8]=1.[N+]([O-])([O-])=O.[Ce+4].[NH4+].[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.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[CH:15]=[CH:14][C:10]([C:11]([OH:13])=[O:12])=[C:9]([O:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH:8]=2)[C:24](=[O:31])[C:25]=1[O:29][CH3:30]

Participants

6

Reactant 3

HCID 180504Ceric ammonium nitrateHCID 9869224Ammonium cerium (IV) nitrateHCID 10275809HCID 10275809, compound

Product 1

HCID 22054338HCID 22054338, compoundYield 64.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent

Procedure

4-(3,4,5,6-Tetramethoxy-2-methylbenzyl)-2-benzyloxybenzoic acid (312 mg, 0.6902 mmol) was dissolved in a mixed solution of acetonitrile (15 ml) and water (5 ml) and after adding thereto ammonium cerium(IV) nitrate (hereinafter simply referred to as “CAN”) (946 mg, 1.7262 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 (187 mg, 0.4431 mmol, 64%).

Workup

  1. additionafter adding
  2. customat room temperature
  3. extractionextracted with ether
  4. washThe extract was washed with water
  5. customdried
  6. customthe solvent was removed by distillation
  7. customThe residue was recrystallized from ether

Sources & evidence

ORD record
ord-ce908970edfd48668a4df71e6454249e
Source dataset
uspto-grants-2006_06
Patent number
US07064124B2

Reaction notes

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