m-Chloroperbenzoic acid → 2-(2-Methoxymethoxyethyl)oxirane

HRID 856138Notes

Reaction equation

HRID 856138 reaction equation
ClC1C=[CH:6][CH:5]=[C:4]([C:8]([O:10]O)=O)C=1.[CH3:12][O:13][CH2:14][O:15]CCC=C>C(Cl)Cl>[CH3:12][O:13][CH2:14][O:15][CH2:6][CH2:5][CH:4]1[CH2:8][O:10]1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 14023234But-3-enoxymethoxymethane

Product 1

HCID 148626352-(2-Methoxymethoxyethyl)oxiraneYield 86.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

m-Chloroperbenzoic acid (20.6 g, 95.6 mmol) was gradually added to a solution of 4-methoxymethoxy-1-butene (10.46 g, 90.1 mmol) in methylene chloride (250 ml) while cooling in an ice-bath, the mixture was stirred at room temperature for 6 hours. The reaction mixture was filtered, and the filtrate was washed with a 10% sodium sulfide aqueous solution and sodium hydrogencarbonate aqueous solution, dried over magnesium sulfate. After filtration, the filtrate was concentrated under reduced pressure to afford 2-(2-methoxymethoxyethyl)oxirane (10.3 g, 86%) as a colorless oil.

Workup

  1. temperaturewhile cooling in an ice-bath
  2. filtrationThe reaction mixture was filtered
  3. washthe filtrate was washed with a 10% sodium sulfide aqueous solution and sodium hydrogencarbonate aqueous solution
  4. dry with materialdried over magnesium sulfate
  5. filtrationAfter filtration
  6. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-0708796f5979443e8c236fe0b0d1f2d5
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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