Water → 2-Methoxymethoxymethyl-2-methyloxirane

HRID 856093Notes

Reaction equation

HRID 856093 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[CH3:12][O:13][CH2:14][O:15][CH2:16][C:17]([CH3:19])=[CH2:18].C(=O)([O-])O.[Na+].O>C(Cl)Cl>[CH3:12][O:13][CH2:14][O:15][CH2:16][C:17]1([CH3:19])[CH2:18][O:9]1

Participants

6

Reactant 4

HCID 962WaterHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 136946203-Methoxymethoxy-2-methyl-1-propene

Product 1

HCID 230811692-Methoxymethoxymethyl-2-methyloxiraneYield 62%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

m-Chloroperbenzoic acid (22.7 g, 92 mmol) was gradually added to a solution of 3-methoxymethoxy-2-methyl-1-propene (9.7 g, 84 mmol) prepared in Reference Example 176 in methylene chloride (200 ml) while cooling in an ice-bath and the mixture was stirred at room temperature for 6 hours. Sodium hydrogencarbonate (14.1 g, 168 mmol), water and methylene chloride were added to the reaction mixture, which was stirred for a while. The organic layer was separated, washed with sodium hydrogencarbonate aqueous solution, sodium thiosulfate aqueous solution and then sodium hydrogencarbonate aqueous solution, and dried over magnesium sulfate. After filtration, the filtrate was concentrated under reduced pressure to afford 2-methoxymethoxymethyl-2-methyloxirane (6.8 g, yield 62%) as a green-colored oil.

Workup

  1. temperaturewhile cooling in an ice-bath
  2. stirringwas stirred for a while
  3. customThe organic layer was separated
  4. washwashed with sodium hydrogencarbonate aqueous solution, sodium thiosulfate aqueous solution
  5. dry with materialsodium hydrogencarbonate aqueous solution, and dried over magnesium sulfate
  6. filtrationAfter filtration
  7. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-6c93ef7b34fe463daa42541d9206b255
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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