2-Methoxyethanol → Ethanol

HRID 1090596Notes

Reaction equation

HRID 1090596 reaction equation
[Na].[H][H].Cl[C:5]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][C:8]([N+:14]([O-:16])=[O:15])=[CH:7][N:6]=1.[Cl-].[NH4+].[CH3:19][O:20][CH2:21][CH2:22][OH:23]>C(O)CO>[CH3:19][O:20][CH2:21][CH2:22][O:23][C:5]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][C:8]([N+:14]([O-:16])=[O:15])=[CH:7][N:6]=1.[CH2:21]([OH:20])[CH3:22]

Participants

8

Reactant 5

HCID 80192-MethoxyethanolHCID 25517Ammonium ChlorideHCID 757382-Chloro-3,5-dinitropyridineHCID 5360545SodiumHCID 178418361HCID 178418361, compound

Product 2

HCID 702EthanolYield 82%HCID 19913415HCID 19913415, compound

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Procedure

3.22 g (140 mmol) of metallic sodium was added to 70 ml of ethylene glycol monomethyl ether under ice-cooling and the mixture was stirred until no more hydrogen gas was produced. To the solution was dropwise added 25.0 g (123 mmol) of 2-chloro-3,5-dinitropyridine in 30 ml of ethylene glycol under ice-cooling over 5 minutes. After stirring for 30 minutes, the mixture was charged into 500 ml of saturated aqueous solution of ammonium chloride, followed by extraction with 400 ml of chloroform. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. Solvent was evaporated under reduced pressure to obtain yellow crystals. 24.5 g (101 mmol) of light yellow prismal crystals of the title compound was obtained by recrystallization from ethanol (yield: 82%).

Workup

  1. temperaturecooling
  2. customwas produced
  3. temperaturecooling over 5 minutes
  4. extractionfollowed by extraction with 400 ml of chloroform
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customSolvent was evaporated under reduced pressure
  8. customto obtain yellow crystals

Sources & evidence

ORD record
ord-5aff577d6cfa432eb28df96fc01c5987
Source dataset
uspto-grants-1992_01
Patent number
US05082467

Reaction notes

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