m-Chloroperbenzoic acid → Methyl 2-(8,9-epoxynonyloxy)-2-methylpropionate

HRID 857204Notes

Reaction equation

HRID 857204 reaction equation
[CH3:1][C:2]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH:16]=[CH2:17])([CH3:7])[C:3]([O:5][CH3:6])=[O:4].ClC1C=CC=C(C(OO)=[O:26])C=1>C(Cl)Cl>[O:26]1[CH2:17][CH:16]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][O:8][C:2]([CH3:1])([CH3:7])[C:3]([O:5][CH3:6])=[O:4]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 21866680Methyl 2-methyl-2-(8-nonenyloxy)propionate

Product 1

HCID 21866634Methyl 2-(8,9-epoxynonyloxy)-2-methylpropionateYield 101.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methyl 2-methyl-2-(8-nonenyloxy)propionate (40 g) was dissolved in 320 ml of methylene chloride, and 40.8 g of 70% 3-chloroperbenzoic acid was added with stirring under ice-cooling, and the mixture was stirred for 15 hours at room temperature. The reaction solution was filtrated to remove insolubles, and the filtrate was concentrated. The residue was dissolved in n-hexane and washed 4 times with aqueous 10% potassium carbonate solution, washed with water, dried over anhydrous magnesium sulfate and concentrated to give 43.2 g of the objective compound as colorless oil.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred for 15 hours at room temperature
  3. filtrationThe reaction solution was filtrated
  4. customto remove insolubles
  5. concentrationthe filtrate was concentrated
  6. dissolutionThe residue was dissolved in n-hexane
  7. washwashed 4 times with aqueous 10% potassium carbonate solution
  8. washwashed with water
  9. dry with materialdried over anhydrous magnesium sulfate
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-d1fc5c6e47d94ad5a7bcb91f05ffa562
Source dataset
uspto-grants-2006_12
Patent number
US07144906B2

Reaction notes

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