Sodium Hydroxide → 2-{3-[2-(2-Methoxyethoxy)ethoxy]phenyl}oxirane

HRID 23656

Reaction equation

HRID 23656 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][O:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=1)[CH:12]=[O:13].[CH3:17]OS([O-])(=O)=O.C[S+](C)C.[OH-].[Na+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C(Cl)Cl.O.CCOCC.[Cl-].[Na+].O>[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][O:8][C:9]1[CH:10]=[C:11]([CH:12]2[CH2:17][O:13]2)[CH:14]=[CH:15][CH:16]=1

Participants

9

Reactant 3

HCID 14798Sodium HydroxideHCID 2760871Trimethylsulfonium methyl sulfateHCID 225743243-[2-(2-Methoxyethoxy)ethoxy]benzaldehyde

Product 1

HCID 225743822-{3-[2-(2-Methoxyethoxy)ethoxy]phenyl}oxiraneYield 126.9%

Reagents, catalysts & solvents 5

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a stirred solution of 1.32 g of 3-[2-(2-methoxyethoxy)ethoxy]benzaldehyde and 15 mg of tetra-n-butylammonium bromide in 15 ml of CH2Cl2 is added a solution of 2.4 g of trimethylsulfonium methylsulfate in 4 ml of water, followed by 10 ml of 50% NaOH. The mixture is stirred and refluxed for 4 h, then cooled, diluted with ether and brine, and filtered. The organic phase is washed with brine, dried (MgSO4), and concentrated under reduced pressure to provide 1.78 g of the title compound as a pale yellow oil.

Workup

  1. temperaturerefluxed for 4 h
  2. temperaturecooled
  3. filtrationfiltered
  4. washThe organic phase is washed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-212bfc66156440dcb496d984dc7e2eed
Source dataset
uspto-grants-2005_02
Patent number
US06852731B2

Linked notes

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