Sodium Hydroxide → 2-Methoxyimino-3,3-ethylenedioxybutyric acid

HRID 1982012Notes

Reaction equation

HRID 1982012 reaction equation
[OH-].[Na+].[CH3:3][O:4][N:5]=[C:6]([C:12]1([O:17][CH2:16][CH2:15][O:14]1)[CH3:13])[C:7]([O:9]CC)=[O:8]>C(O)C>[CH3:3][O:4][N:5]=[C:6]([C:12]1([O:14][CH2:15][CH2:16][O:17]1)[CH3:13])[C:7]([OH:9])=[O:8]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 54382027Ethyl 2-methoxyimino-3,3-ethylenedioxybutyrate

Product 1

HCID 544524052-Methoxyimino-3,3-ethylenedioxybutyric acidYield 79.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1N Aqueous sodium hydroxide (130 ml) was added to a solution of ethyl 2-methoxyimino-3,3-ethylenedioxybutyrate (syn isomer, 25.7 g) in ethanol (150 ml), and stirred at ambient temperature overnight. The resultant solution was concentrated under reduced pressure. The residue was dissolved in a saturated aqueous solution of sodium chloride (80 ml) and washed with diethyl ether. Diethyl ether (100 ml) was added to the aqueous solution, adjusted to pH 1 with 10% hydrochloric acid and the diethyl ether layer was separated. The aqueous layer was extracted with diethyl ether (50 ml) twice. The diethyl ether layer and the extracts were combined, washed with a saturated aqueous solution of sodium chloride and dried over magnesium sulfate. After evaporating the solvent, the residue was crystallized and washed with n-hexane. The precipitates were collected by filtration and dried to give 2-methoxyimino-3,3-ethylenedioxybutyric acid (syn isomer, 17.7 g).

Workup

  1. concentrationThe resultant solution was concentrated under reduced pressure
  2. dissolutionThe residue was dissolved in a saturated aqueous solution of sodium chloride (80 ml)
  3. washwashed with diethyl ether
  4. additionDiethyl ether (100 ml) was added to the aqueous solution
  5. customthe diethyl ether layer was separated
  6. extractionThe aqueous layer was extracted with diethyl ether (50 ml) twice
  7. washwashed with a saturated aqueous solution of sodium chloride
  8. dry with materialdried over magnesium sulfate
  9. customAfter evaporating the solvent
  10. customthe residue was crystallized
  11. washwashed with n-hexane
  12. filtrationThe precipitates were collected by filtration
  13. customdried

Sources & evidence

ORD record
ord-5408a225a9a649f3af4b73bf2a4d4e36
Source dataset
uspto-grants-1986_06
Patent number
US04594446

Reaction notes

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