Hydrogen Peroxide → 4-{[3-Methyl-6-(methyloxy)-2-phenyl-1-naphthalenyl]oxy}phenol

HRID 1993011Notes

Reaction equation

HRID 1993011 reaction equation
[CH3:1][C:2]1[C:3]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[C:4]([O:14][C:15]2[CH:22]=[CH:21][C:18](C=O)=[CH:17][CH:16]=2)[C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([O:12][CH3:13])=[CH:7][CH:6]=2.OO.C([O-])(O)=[O:32].[Na+]>CO.OS(O)(=O)=O.CCOC(C)=O>[CH3:1][C:2]1[C:3]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)=[C:4]([O:14][C:15]2[CH:16]=[CH:17][C:18]([OH:32])=[CH:21][CH:22]=2)[C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([O:12][CH3:13])=[CH:7][CH:6]=2

Participants

7

Reactant 3

HCID 784Hydrogen PeroxideHCID 516892Sodium BicarbonateHCID 860871594-[(6-Methoxy-3-methyl-2-phenyl-1-naphthyl)oxy]benzaldehyde

Product 1

HCID 685394164-{[3-Methyl-6-(methyloxy)-2-phenyl-1-naphthalenyl]oxy}phenolYield 61%

Reagents, catalysts & solvents 3

HCID 1118Sulfuric AcidCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-{[3-methyl-6-(methyloxy)-2-phenyl-1-naphthalenyl]oxy}benzaldehyde (8) (2.00 g, 5.43 mmol) in MeOH (40 mL) were added an aqueous solution of, 30-40% by weight, H2O2 (5.0 mL) and a few drops (10-12) of conc. H2SO4. The resultant mixture was stirred for 24 h. Reaction mixture was neutralized with saturated aqueous NaHCO3 and then diluted with EtOAc (200 mL). Reaction mixture was washed with water (2×30 mL), brine (1×30 mL), dried (Na2SO4), and concentrated under reduced pressure to afford the crude product. The product was purified by SiO2 column chromatography using hexanes:EtOAc (9:1 to 4:1) as an eluent to give 1.180 g (61%) of the title compound (233) as a white foam. The 1H NMR and mass spectral data are consistent with the data reported in Example 41 (Step 1).

Workup

  1. customReaction mixture
  2. customReaction mixture
  3. washwas washed with water (2×30 mL), brine (1×30 mL)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated under reduced pressure
  6. customto afford the crude product
  7. customThe product was purified by SiO2 column chromatography

Sources & evidence

ORD record
ord-045c10c523e34903a0a61490bd7b68fe
Source dataset
uspto-grants-2010_01
Patent number
US07649093B2

Reaction notes

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