Hydrogen Peroxide → Methyl (R)-2-(4-acetoxyphenoxy)propionate

HRID 2392911Notes

Reaction equation

HRID 2392911 reaction equation
OO.C([C:6]1[CH:18]=[CH:17][C:9]([O:10][C@H:11]([CH3:16])[C:12]([O:14][CH3:15])=[O:13])=[CH:8][CH:7]=1)(=O)C.S([O-])([O-])=O.[Na+].[Na+]>O.C(O)=O>[C:12]([O:14][C:6]1[CH:7]=[CH:8][C:9]([O:10][C@H:11]([CH3:16])[C:12]([O:14][CH3:15])=[O:13])=[CH:17][CH:18]=1)(=[O:13])[CH3:11]

Participants

6

Reactant 3

HCID 784Hydrogen Peroxide2×HCID 24437Sodium SulfiteHCID 14717335Methyl (R)-2-(4-acetylphenoxy)propionate

Product 1

HCID 54186344Methyl (R)-2-(4-acetoxyphenoxy)propionateYield 96%

Reagents, catalysts & solvents 2

HCID 284Formic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
35 °C

Procedure

54.4 g (0.48 mol) of a 30% strength solution of hydrogen peroxide in water was added dropwise to the solution of 88.93 g (0.4 mol) of methyl (R)-2-(4-acetylphenoxy)propionate in 356 g of formic acid at 35° C. over the course of 1 h. After stirring at 35° C. for 5 hours, the excess hydrogen peroxide was decomposed with 5 g of sodium sulfite. The mixture was finally concentrated under reduced pressure and subjected to a short-path distillation at 150°-160° C. under 0.5 mbar. Yield: 96% (94-95% enantiomeric excess).

Workup

  1. concentrationThe mixture was finally concentrated under reduced pressure
  2. distillationsubjected to a short-path distillation at 150°-160° C. under 0.5 mbar

Sources & evidence

ORD record
ord-5185d7b7703a43ffa23c4a0b281716a5
Source dataset
uspto-grants-1998_09
Patent number
US05801272

Reaction notes

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