Hydrogen Peroxide → 3-(3,4,5,6-Tetramethoxy-2-methylbenzyl)-2-benzyloxybenzoic Acid

HRID 1245158Notes

Reaction equation

HRID 1245158 reaction equation
[CH3:1][O:2][C:3]1[C:4]([CH3:32])=[C:5]([C:23]([O:30][CH3:31])=[C:24]([O:28][CH3:29])[C:25]=1[O:26][CH3:27])[CH2:6][C:7]1[C:8]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[C:9]([CH:12]=[CH:13][CH:14]=1)[CH:10]=[O:11].P([O-])(O)(O)=[O:34].[Na+].Cl[O-].[Na+].OO>C(#N)C.O>[CH3:1][O:2][C:3]1[C:4]([CH3:32])=[C:5]([C:23]([O:30][CH3:31])=[C:24]([O:28][CH3:29])[C:25]=1[O:26][CH3:27])[CH2:6][C:7]1[C:8]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[C:9]([CH:12]=[CH:13][CH:14]=1)[C:10]([OH:34])=[O:11]

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 21919151HCID 21919151, compoundHCID 23665760Sodium HypochloriteHCID 23672064Monosodium phosphate

Product 1

HCID 219192093-(3,4,5,6-Tetramethoxy-2-methylbenzyl)-2-benzyloxybenzoic AcidYield 98.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of 3-(3,4,5,6-tetramethoxy-2-methylbenzyl)-2-benzyloxybenzaldehyde (1.87 g, 4.28 mmol) in acetonitrile (12.0 ml) were added an aqueous solution (7.0 ml) of sodium dihydrogen phosphate (4.01 g, 33.42 mmol), an aqueous solution (7.0 ml) of sodium hypochlorite (1.74 g, 19.33 mmol) and an aqueous hydrogen peroxide (1.89 ml, 30%) and the mixture was stirred at room temperature for 5 hours. The reaction solution was diluted with water and extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium hydrosulfite (Na2S2O4) and a saturated saline, dried and concentrated to give the title compound (1.90 g, 4.20 mmol, 98%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with a saturated aqueous solution of sodium hydrosulfite (Na2S2O4)
  3. customa saturated saline, dried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-fb6a4b37562045548124ac3df07fca59
Source dataset
uspto-grants-2006_10
Patent number
US07122543B2

Reaction notes

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