Ethylene Glycol → Ethyl 2-methoxyimino-3,3-ethylenedioxybutyrate

HRID 1982011Notes

Reaction equation

HRID 1982011 reaction equation
[CH3:1][O:2][N:3]=[C:4]([C:10](=[O:12])[CH3:11])[C:5]([O:7][CH2:8][CH3:9])=[O:6].[CH2:13](O)[CH2:14][OH:15]>C1C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH3:1][O:2][N:3]=[C:4]([C:10]1([O:15][CH2:14][CH2:13][O:12]1)[CH3:11])[C:5]([O:7][CH2:8][CH3:9])=[O:6]

Participants

5

Reactant 2

HCID 174Ethylene GlycolHCID 43493Ethyl (2Z)-2-methoxyimino-3-oxo-butanoate

Product 1

HCID 54382027Ethyl 2-methoxyimino-3,3-ethylenedioxybutyrateYield 70%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 241BenzeneSolvent

Procedure

A solution of ethyl 2-methoxyimino-3-oxobutyrate (syn isomer 17.3 g), ethylene glycol (12.4 g) and p-toluenesulfonic acid (0.5 g) in benzene (260 ml) was heated under reflux while removing water. The resultant solution was washed with a saturated aqueous solution of sodium bicarbonate and a saturated aqueous solution of sodium chloride in turn and dried over magnesium sulfate. After evaporating the solvent from the solution, the residue was distilled under reduced pressure to give ethyl 2-methoxyimino-3,3-ethylenedioxybutyrate (syn isomer, 15.2 g), bp 97° to 102° C./4 mmHg.

Workup

  1. temperatureunder reflux
  2. customwhile removing water
  3. washThe resultant solution was washed with a saturated aqueous solution of sodium bicarbonate
  4. dry with materiala saturated aqueous solution of sodium chloride in turn and dried over magnesium sulfate
  5. customAfter evaporating the solvent from the solution
  6. distillationthe residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-4b9a4c7199794c8197963a44a514e79f
Source dataset
uspto-grants-1986_06
Patent number
US04594446

Reaction notes

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