Hydrogen Peroxide → HCID 28825277, compound

HRID 130736Notes

Reaction equation

HRID 130736 reaction equation
[CH:1]([C:3]1[CH:17]=[CH:16][C:6]([O:7][C:8]2[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][CH:9]=2)=[CH:5][CH:4]=1)=[O:2].C(=O)([O-])[O-:19].[K+].[K+].OO>O>[CH:1]([C:3]1[CH:17]=[CH:16][C:6]([O:7][C:8]2[CH:15]=[CH:14][C:11]([C:12]([NH2:13])=[O:19])=[CH:10][CH:9]=2)=[CH:5][CH:4]=1)=[O:2]

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 11430Potassium CarbonateHCID 6138064-(4-Formylphenoxy)benzonitrile

Product 1

HCID 28825277HCID 28825277, compoundYield 81.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Combine 4-(4-Formyl-phenoxy)-benzonitrile (3.6 g, 16.1 mmol), dimethylsufoxide (25 mL), potassium carbonate (2.1 g, 15.2 mmol), and 3 mL of 30% hydrogen peroxide solution. Stir 18 h at ambient temperature. Dilute with 100 mL of water, extract with ethyl acetate (3×100 mL). Wash the organic phase with 100 mL of water, and 50 mL of brine. Dry the organic phase over sodium sulfate, filter, and concentrate under vacuum. Purify via aBiotage Flash 40L system using 75:25 hexanes/ethyl acetate as eluting solvent to give 3.0 g (77%) of the title compound: 1H NMR (chloroform-d): 9.95 (s, 1H), 7.88 (m, 4H), 7.12 (m, 4H), 5.29-5.14 (br m, 2H).

Workup

  1. extractionextract with ethyl acetate (3×100 mL)
  2. washWash the organic phase with 100 mL of water, and 50 mL of brine
  3. dry with materialDry the organic phase over sodium sulfate
  4. filtrationfilter
  5. concentrationconcentrate under vacuum
  6. customPurify via aBiotage Flash 40L system
  7. washas eluting solvent

Sources & evidence

ORD record
ord-1fba653bee1c49229ab79ccd2feef591
Source dataset
uspto-grants-2008_06
Patent number
US07381719B2

Reaction notes

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