Ethylene Glycol → Ethyl 2-methoxyimino-3,3-ethylenedioxy-4-chlorobutyrate

HRID 1982013Notes

Reaction equation

HRID 1982013 reaction equation
[CH3:1][O:2][N:3]=[C:4]([C:10](=[O:13])[CH2:11][Cl:12])[C:5]([O:7][CH2:8][CH3:9])=[O:6].[CH2:14](O)[CH2:15][OH:16].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH3:1][O:2][N:3]=[C:4]([C:10]1([O:16][CH2:15][CH2:14][O:13]1)[CH2:11][Cl:12])[C:5]([O:7][CH2:8][CH3:9])=[O:6]

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 3017525Ethyl 4-chloro-2-(methoxyimino)-3-oxobutanoate

Product 1

HCID 54025463Ethyl 2-methoxyimino-3,3-ethylenedioxy-4-chlorobutyrateYield 49.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of ethyl 2-methoxyimino-3-oxo-4-chlorobutyrate (syn isomer, 41 g), ethylene glycol (24.6 g), p-toluenesulfonic acid (2.0 g) and toluene (250 ml) was heated for 20 hours under reflux while removing water. The reaction mixture was cooled to ambient temperature, washed with a saturated aqueous solution of sodium bicarbonate, a saturated aqueous solution of sodium chloride in turn, dried over magnesium sulfate and then the solvents were removed. The residue was distilled under reduced pressure to give ethyl 2-methoxyimino-3,3-ethylenedioxy-4-chlorobutyrate (syn isomer, 24.4 g), bp 103°-110° C./2 mmHg.

Workup

  1. temperaturewas heated for 20 hours
  2. temperatureunder reflux
  3. customwhile removing water
  4. washwashed with a saturated aqueous solution of sodium bicarbonate
  5. dry with materiala saturated aqueous solution of sodium chloride in turn, dried over magnesium sulfate
  6. customthe solvents were removed
  7. distillationThe residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-e0fd25559cc64aaa9a5943fe0f1ebeba
Source dataset
uspto-grants-1986_06
Patent number
US04594446

Reaction notes

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