Hydrogen Peroxide → HCID 57552550, compound

HRID 1513861Notes

Reaction equation

HRID 1513861 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:17]=[CH:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([O:18][CH3:19])[CH:14]=3)[C:9]=2[O:20][C:21]2[CH:28]=[CH:27][C:24](C=O)=[CH:23][CH:22]=2)[CH:5]=[CH:6][CH:7]=1.OO.S(=O)(=O)(O)[OH:32]>C(OCC)(=O)C.O>[F:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:17]=[CH:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([O:18][CH3:19])[CH:14]=3)[C:9]=2[O:20][C:21]2[CH:22]=[CH:23][C:24]([OH:32])=[CH:27][CH:28]=2)[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 784Hydrogen PeroxideHCID 1118Sulfuric AcidHCID 538840564-[2-(3-Fluoro-phenyl)-6-methoxy-naphthalen-1-yloxy]-benzaldehyde

Product 1

HCID 57552550HCID 57552550, compoundYield 22%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

Charge a 100 mL round-bottom flask with 4-[2-(3-fluoro-phenyl)-6-methoxy-naphthalen-1-yloxy]-benzaldehyde (2.5 g, 6.71 mmol) and ethyl acetate (5 mL). At room temperature add 2 mL of 35% hydrogen peroxide. To this solution slowly add 2 mL of concentrated sulfuric acid. The mixture warms to approximately 40° C. and returns to room temperature where it is stirred for 2 hours. Dilute the reaction with water and ethyl acetate (100 mL) and dry the organic layer over sodium sulfate, filter and concentrate in vacuo. Purify the crude product using radial chromatography eluting with CH2Cl2 to yield 540 mg (22%) of the title compound: mass spectrum (ion spray) m/z=359 (M−H).

Workup

  1. customwarms to approximately 40° C.
  2. additionDilute
  3. dry with materialdry the organic layer over sodium sulfate
  4. filtrationfilter
  5. concentrationconcentrate in vacuo
  6. customPurify the crude product
  7. washeluting with CH2Cl2

Sources & evidence

ORD record
ord-bcc63bc3eede4d7e9133b7e3c48868b7
Source dataset
uspto-grants-2012_07
Patent number
US08217032B2

Reaction notes

Loading…