Hydrogen Peroxide → HCID 22706889, compound

HRID 353027Notes

Reaction equation

HRID 353027 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([O:15]CC2C=CC=CC=2)[C:10]=1[O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:31]O>CC(O)=O.C(Cl)Cl>[CH2:1]([O:8][C:9]1[C:14](=[O:31])[CH:13]=[CH:12][C:11](=[O:15])[C:10]=1[O:23][CH2:24][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 784Hydrogen PeroxideHCID 205433631,1',1''-[Benzene-1,2,3-triyltris(oxymethylene)]tribenzene

Product 1

HCID 22706889HCID 22706889, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 1,2,3-tribenzyloxybenzene 8 (2.0 g, 5.0 mmol) in HOAc (30 mL), K3Fe(CN)6 (0.82 g, 2.5 mmol) and 30% H2O2 (1.3 g, 11.5 mmol) were added and the resulting solution stirred at room temperature for 18 h. The solution was diluted with 50 mL CH2Cl2 and the organic layer subsequently washed with H2O, saturated aqueous NaHCO3 and brine. Drying and concentration resulted in a red oil. Purification by radial chromatography (2 mm thickness, EtOAc/hexane, 1:19, v/v) afforded 9 as a red oil. 1H NMR (CDCl3): δ7.36-7.32 (m, 10 H), 6.58 (s, 2 H), 5.20 (s, 4 H). 13C NMR (CDCl3): δ184.1, 145.2, 136.1, 134.6 128.5, 128.4, 128.1, 75.1. Anal. Calcd for C20H18O4: C, 74.99; H, 5.03. Found: C, 75.04; H, 5.06. HRMS (FAB) calcd for C20H16O4 (M+H+): 320.1049. Found: 320.1059.

Workup

  1. washthe organic layer subsequently washed with H2O, saturated aqueous NaHCO3 and brine
  2. customDrying
  3. concentrationconcentration
  4. customresulted in a red oil
  5. customPurification by radial chromatography (2 mm thickness, EtOAc/hexane, 1:19, v/v)

Sources & evidence

ORD record
ord-96f6f10190f643178b0db865f396d35e
Source dataset
uspto-grants-2004_06
Patent number
US06750049B1

Reaction notes

Loading…