Hydrogen Peroxide → HCID 10921072, compound

HRID 359968Notes

Reaction equation

HRID 359968 reaction equation
C(OO)(=[O:3])C.OO.S(=O)(=O)(O)O.[C:13]([O:16][C:17]1[CH:24]=[CH:23][C:20]([CH:21]=[CH2:22])=[CH:19][CH:18]=1)(=[O:15])[CH3:14].C([O-])(=O)C.[Na+]>S(=O)(=O)(O)O.C(Cl)(Cl)Cl.O.C(O)(=O)C>[C:13]([O:16][C:17]1[CH:24]=[CH:23][C:20]([CH:21]2[O:3][CH2:22]2)=[CH:19][CH:18]=1)(=[O:15])[CH3:14]

Participants

10

Reactant 5

HCID 784Hydrogen Peroxide2×HCID 1118Sulfuric Acid2×HCID 6585Peracetic Acid3×HCID 758214-Ethenylphenyl acetateHCID 517045Sodium Acetate

Product 1

HCID 10921072HCID 10921072, compoundYield 98%

Reagents, catalysts & solvents 4

HCID 1118Sulfuric AcidCatalystHCID 176Acetic AcidSolvent2×HCID 962WaterSolvent2×HCID 6212ChloroformSolvent2×

Procedure

Commercially available peracetic acid (57 g) produced by the oxidation of acetic acid with hydrogen peroxide using sulfuric acid as catalyst, and containing about 35 wt % of peracetic acid, about 19 wt % of water, about 0.6 wt % of hydrogen peroxide, about 1 wt % of sulfuric acid, and the remainder acetic acid, is mixed with chloroform (250 ml) and transferred to a separatory funnel. The upper aqueous layer is discarded and the chloroform layer is dried over magnesium sulfate and filtered to yield a solution containing about 37 wt % of peracetic acid, about 0.6% wt of hydrogen peroxide, and the remainder acetic acid. No more than a trace of sulfuric acid or water is detectable. The solution is added dropwise to an ice cold solution of 4-acetoxystyrene (24.3 g, 0.15 mol) in chloroform (150 ml) containing sodium acetate (5.0 g). After the addition of peracetic acid solution, the reaction mixture is warmed up to room temperature and stirred overnight. The reaction mixture is washed with water (3×200 ml) and saturated sodium bicarbonate solution (3×200 ml), dried over anhydrous magnesium sulfate, filtered, and concentrated in-vacuo to afford an oil characterized by NMR analysis as 4-acetoxystyrene oxide (26.2 g, 98% yield).

Workup

  1. customtransferred to a separatory funnel
  2. dry with materialthe chloroform layer is dried over magnesium sulfate
  3. filtrationfiltered
  4. customto yield a solution
  5. washThe reaction mixture is washed with water (3×200 ml) and saturated sodium bicarbonate solution (3×200 ml)
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in-vacuo
  9. customto afford an oil

Sources & evidence

ORD record
ord-b0690a4daaea429f95235211feebaa22
Source dataset
uspto-grants-1991_03
Patent number
US05003115

Reaction notes

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