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

HRID 1992980Notes

Reaction equation

HRID 1992980 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 80%

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) (0.740 g, 2 mmol) in MeOH (20 mL) were added an aqueous solution of 30-40%, by weight, H2O2 (0.60 mL) and 2-3 drops of conc. H2SO4. The resultant mixture was stirred for over night. The reaction mixture was neutralized with sat. NaHCO3 and then diluted with EtOAc (100 mL). The organic layer was washed with water, brine, 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 0.570 g (80%) of the title compound (233) as a white foam. IR (film) 3415, 1633, 1599, 1503, 1198 cm-1. 1H NMR (400 MHz, CDCl3): δ 7.80 (d, J=9.2 Hz, 1H), 7.53 (s, 1H), 7.29-7.22 (m, 3H), 7.14-7.11 (m, 3H), 7.08 and 7.03 (dd, J1=9.2 Hz, J2=2.4 Hz, 1H), 6.53-6.50 (m, 2H), 6.45-6.42 (m, 2H), 3.93 (s, 3H), 2.23 (s, 3H). LCMS (ES) m/z 357.01 (M+H)+.

Workup

  1. washThe organic layer was washed with water, brine
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated under reduced pressure
  4. customto afford the crude product
  5. customThe product was purified by SiO2 column chromatography

Sources & evidence

ORD record
ord-eb52850d19204a4a8780a84d35aa85f1
Source dataset
uspto-grants-2010_01
Patent number
US07649093B2

Reaction notes

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