Hydrogen Peroxide → 1-(4-Hydroxyphenoxy)-2-(3-Methoxyphenyl)-6-Methoxynaphthalene

HRID 2414302Notes

Reaction equation

HRID 2414302 reaction equation
C([C:3]1[CH:29]=[CH:28][C:6]([O:7][C:8]2[C:17]3[C:12](=[CH:13][C:14]([O:18][CH3:19])=[CH:15][CH:16]=3)[CH:11]=[CH:10][C:9]=2[C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([O:26][CH3:27])[CH:21]=2)=[CH:5][CH:4]=1)=O.OO.[OH:32]S(O)(=O)=O.C([O-])(O)=O.[Na+]>CO>[OH:32][C:3]1[CH:29]=[CH:28][C:6]([O:7][C:8]2[C:17]3[C:12](=[CH:13][C:14]([O:18][CH3:19])=[CH:15][CH:16]=3)[CH:11]=[CH:10][C:9]=2[C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([O:26][CH3:27])[CH:21]=2)=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 120741741-(4-Formylphenoxy)-2-(3-Methoxyphenyl)-6-Methoxynaphthalene

Product 1

HCID 120741751-(4-Hydroxyphenoxy)-2-(3-Methoxyphenyl)-6-Methoxynaphthalene

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

2.3 g (6 mmol) of 1-(4-formylphenoxy)-2-(3-methoxyphenyl)-6-methoxynaphthalene was suspended in 15 mL of MeOH and 1.7 mL (9 mmol) of 30% H2O2 was added. To the stirring mixture, 0.76 mL of conc. H2SO4 was slowly added. An additional 30 mL of MeOH was added and the reaction was allowed to proceed for forty-eight hours. The reaction was neutralized with NaHCO3 solution and extracted with CHCl3. The CHCl3 was washed with brine, dried with Na2SO4, and chromatographed on a silica gel column eluted with CHCl3. This yielded 1.6 g of the title compound as a tan amorphous powder, mp 125-126° C.

Workup

  1. waitto proceed for forty-eight hours
  2. extractionextracted with CHCl3
  3. washThe CHCl3 was washed with brine
  4. dry with materialdried with Na2SO4
  5. customchromatographed on a silica gel column
  6. washeluted with CHCl3

Sources & evidence

ORD record
ord-3bf05de9265c4fe3a047ce7287bb5245
Source dataset
uspto-grants-2004_11
Patent number
US06812244B2

Reaction notes

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