Benzene → Ethyl 2-methoxyimino-3,3-ethylenedioxybutyrate

HRID 1982009Notes

Reaction equation

HRID 1982009 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].[CH:13]1[CH:18]=CC=CC=1.C1(C)C=CC(S(O)(=O)=[O:26])=CC=1>C(O)CO>[CH3:1][O:2][N:3]=[C:4]([C:10]1([O:26][CH2:13][CH2:18][O:12]1)[CH3:11])[C:5]([O:7][CH2:8][CH3:9])=[O:6]

Participants

5

Reactant 3

HCID 241BenzeneHCID 6101p-Toluenesulfonic acidHCID 43493Ethyl (2Z)-2-methoxyimino-3-oxo-butanoate

Product 1

HCID 54382027Ethyl 2-methoxyimino-3,3-ethylenedioxybutyrateYield 85.5%

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Procedure

To a solution of ethyl 2-methoxyimino-3-oxobutyrate (syn isomer, 200 g) in ethylene glycol (179 g) were added dried benzene (3 l) and p-toluenesulfonic acid (6 g), and the mixture was heated for 20 hours under reflux while removing water azeotropically. The reaction mixture was cooled to ambient temperature, washed with water, a saturated aqueous solution of sodium bicarbonade, water and a saturated aqueous solution of sodium chloride in turn, dried over magnesium sulfate and then filtered. After the filtrate was evaporated, the residual oil was distilled under reduced pressure to give ethyl 2-methoxyimino-3,3-ethylenedioxybutyrate (syn isomer), bp 89.5°-91° C./0.6 mmHg, in 85.5% yield.

Workup

  1. temperaturethe mixture was heated for 20 hours
  2. temperatureunder reflux
  3. customwhile removing water azeotropically
  4. washwashed with water
  5. dry with materiala saturated aqueous solution of sodium bicarbonade, water and a saturated aqueous solution of sodium chloride in turn, dried over magnesium sulfate
  6. filtrationfiltered
  7. customAfter the filtrate was evaporated
  8. distillationthe residual oil was distilled under reduced pressure

Sources & evidence

ORD record
ord-b948b215bde84f1c9cf429a41efa3a27
Source dataset
uspto-grants-1986_06
Patent number
US04594446

Reaction notes

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