Hydrogen Peroxide → HCID 18348570, compound

HRID 2268501Notes

Reaction equation

HRID 2268501 reaction equation
[CH3:1][O:2][C:3]1[C:11]([O:12][CH3:13])=[C:10]([O:14][CH3:15])[C:9]([O:16][CH3:17])=[C:8]2[C:4]=1[CH2:5][C:6]([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH:31]=[O:32])([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:7]2.P([O-])(O)(O)=[O:34].[Na+].OO.Cl([O-])=O.[Na+].S([O-])([O-])=O.[Na+].[Na+]>O.C(#N)C>[CH3:17][O:16][C:9]1[C:10]([O:14][CH3:15])=[C:11]([O:12][CH3:13])[C:3]([O:2][CH3:1])=[C:4]2[C:8]=1[CH2:7][C:6]([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][C:31]([OH:34])=[O:32])([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:5]2

Participants

8

Reactant 5

HCID 784Hydrogen PeroxideHCID 24437Sodium SulfiteHCID 18348548HCID 18348548, compoundHCID 23668197Sodium ChloriteHCID 23672064Monosodium phosphate

Product 1

HCID 18348570HCID 18348570, compoundYield 240.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent

Procedure

To a mixture of 8-(4,5,6,7-tetramethoxy-2-phenylindan-2-yl)octanal (985 mg), sodium dihydrogenphosphate (72.6 mg), 30% hydrogen peroxide (0.435 ml), acetonitrile (10 ml), and water (4 ml) was dropwise added a solution of sodium chlorite (80%, 355 mg) in water (14 ml) with cooling with ice in 30 min. After the reaction mixture was stirred for 30 min, aqueous sodium sulfite to the reaction mixture, which was then made acidic with 1N hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride and dried. The solvent was removed in vacuo. The residue was purified by silica gel column chromatography (hexane to hexane:ethyl acetate=1:2) to yield the entitled compound (665 mg) as an oil.

Workup

  1. temperaturewith cooling with ice in 30 min
  2. extractionmade acidic with 1N hydrochloric acid and extracted with ethyl acetate
  3. washThe organic layer was washed with saturated aqueous sodium chloride
  4. customdried
  5. customThe solvent was removed in vacuo
  6. customThe residue was purified by silica gel column chromatography (hexane to hexane:ethyl acetate=1:2)

Sources & evidence

ORD record
ord-e665c99f8cba4e1ca7f4a20d29778cf2
Source dataset
uspto-grants-2001_12
Patent number
US06326369B1

Reaction notes

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