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

HRID 463387Notes

Reaction equation

HRID 463387 reaction equation
[OH:1][N:2]=[C:3]([C:9](=[O:11])[CH3:10])[C:4]([O:6][CH2:7][CH3:8])=[O:5].[CH2:12](O)[CH2:13][OH:14]>C1(C)C=CC(S(O)(=O)=O)=CC=1.C1C=CC=CC=1>[OH:1][N:2]=[C:3]([C:9]1([O:14][CH2:13][CH2:12][O:11]1)[CH3:10])[C:4]([O:6][CH2:7][CH3:8])=[O:5]

Participants

5

Reactant 2

HCID 174Ethylene GlycolHCID 178472877HCID 178472877, compound

Product 1

HCID 86738086Ethyl 2-hydroxyimino-3,3-ethylenedioxybutyrateYield 55.8%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 241BenzeneSolvent

Procedure

A mixture of ethyl 2-hydroxyimino-3-oxobutyrate (syn isomer, 10 g), ethylene glycol (19.75 g) and p-toluenesulfonic acid (0.3 g) and dried benzene (150 ml) was heated for 2 hours under reflux while removing water azeotropically. The reaction mixture was washed with water (50 ml), a saturated aqueous solution of sodium bicarbonate (50 ml), water (50 ml) and a saturated aqueous solution of sodium chloride (50 ml) in turn, dried over magnesium sulfate and then filtered. The filtrate was evaporated to give an oil of ethyl 2-hydroxyimino-3,3-ethylenedioxybutyrate (syn isomer, 7.12 g). (Yield: 55.1%).

Workup

  1. temperaturewas heated for 2 hours
  2. temperatureunder reflux
  3. customwhile removing water azeotropically
  4. washThe reaction mixture was washed with water (50 ml)
  5. dry with materiala saturated aqueous solution of sodium bicarbonate (50 ml), water (50 ml) and a saturated aqueous solution of sodium chloride (50 ml) in turn, dried over magnesium sulfate
  6. filtrationfiltered
  7. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-59219cb803b241e3a1b8fb8f97a31b9f
Source dataset
uspto-grants-1985_05
Patent number
US04518774

Reaction notes

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