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

HRID 1830223Notes

Reaction equation

HRID 1830223 reaction equation
P([O-])(O)(O)=O.[Na+].Cl([O-])=O.[Na+].[OH:11]O.[CH3:13][O:14][C:15]1[C:16]([CH3:44])=[C:17]([C:35]([O:42][CH3:43])=[C:36]([O:40][CH3:41])[C:37]=1[O:38][CH3:39])[CH2:18][C:19]1[C:20]([O:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[C:21]([CH:24]=[CH:25][CH:26]=1)[CH:22]=[O:23]>O.C(#N)C>[CH3:13][O:14][C:15]1[C:16]([CH3:44])=[C:17]([C:35]([O:42][CH3:43])=[C:36]([O:40][CH3:41])[C:37]=1[O:38][CH3:39])[CH2:18][C:19]1[C:20]([O:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[C:21]([CH:24]=[CH:25][CH:26]=1)[C:22]([OH:11])=[O:23]

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 21919151HCID 21919151, compoundHCID 23668197Sodium ChloriteHCID 23672064Monosodium phosphate

Product 1

HCID 219192093-(3,4,5,6-Tetramethoxy-2-methylbenzyl)-2-benzyloxybenzoic AcidYield 98%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

An aqueous solution (7 ml) of sodium dihydrogenphosphate (4.01 g, 33.42 mmol), an aqueous solution (7 ml) of sodium chlorite (1.74 g, 19.33 mmol) and aqueous hydrogen peroxide (1.89 ml, 30%) were added to an acetonitrile solution (12 ml) of 3-(3,4,5,6-tetramethoxy-2-methylbenzyl)-2-benzyloxybenzaldehyde (1.87 g, 4.28 mmol) and the resulting solution was stirred at room temperature for 5 hours. The reaction solution was diluted with water and then extracted with ethyl acetate. The extract was washed with an aqueous saturated sodium hydrosulfite (Na2S2O4) solution and saturated brine, then dried and concentrated to obtain the titled compound (1.90 g, 4.20 mmol, 98%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with an aqueous saturated sodium hydrosulfite (Na2S2O4) solution and saturated brine
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-47f1811f559147b8a08da6acbde6bdd2
Source dataset
uspto-grants-2006_06
Patent number
US07064124B2

Reaction notes

Loading…