Hydrogen Peroxide → 4-[6-Benzyloxy-2-(4-fluoro-phenyl)-naphthalen-1-yloxy]-phenol

HRID 1513867Notes

Reaction equation

HRID 1513867 reaction equation
OS(O)(=O)=O.[OH:6]O.[CH2:8]([O:15][C:16]1[CH:17]=[C:18]2[C:23](=[CH:24][CH:25]=1)[C:22]([O:26][C:27]1[CH:34]=[CH:33][C:30](C=O)=[CH:29][CH:28]=1)=[C:21]([C:35]1[CH:40]=[CH:39][C:38]([F:41])=[CH:37][CH:36]=1)[CH:20]=[CH:19]2)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.O>C(Cl)Cl>[CH2:8]([O:15][C:16]1[CH:17]=[C:18]2[C:23](=[CH:24][CH:25]=1)[C:22]([O:26][C:27]1[CH:28]=[CH:29][C:30]([OH:6])=[CH:33][CH:34]=1)=[C:21]([C:35]1[CH:40]=[CH:39][C:38]([F:41])=[CH:37][CH:36]=1)[CH:20]=[CH:19]2)[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 962WaterHCID 1118Sulfuric AcidHCID 866265284-[6-Benzyloxy-2-(4-fluoro-phenyl) naphthalen-1-yloxy]-benzaldehyde

Product 1

HCID 575525594-[6-Benzyloxy-2-(4-fluoro-phenyl)-naphthalen-1-yloxy]-phenolYield 73%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add 18M H2SO4 (1 mL, 16.8 mmol) dropwise into a solution of H2O2 (1 mL, 9.7 mmol) and 4-[6-benzyloxy-2-(4-fluoro-phenyl)-naphthalen-1-yloxy]-benzaldehyde at 0° C. and stir at room temperature for 12 hours. Add H2O (20 mL) and CH2Cl2 (100 mL). Separate layers and extract the aqueous layer with CH2Cl2 (2×50 mL). Combine the organic layers, dry with magnesium sulfate and concentrate in vacuo to obtain 1.88 g (73%) of the title compound: mass spectrum (ion spray) m/z=435.1 (M−H).

Workup

  1. extractionSeparate layers and extract the aqueous layer with CH2Cl2 (2×50 mL)
  2. dry with materialCombine the organic layers, dry with magnesium sulfate
  3. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-460ab5ef25d647cca91f11715829e293
Source dataset
uspto-grants-2012_07
Patent number
US08217032B2

Reaction notes

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