Hydrochloric Acid → 2-Methoxyimino-3,3-ethylenedioxybutyric acid

HRID 1982010Notes

Reaction equation

HRID 1982010 reaction equation
[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]CC)=[O:6].[OH-].[Na+].Cl>C(O)C>[CH3:1][O:2][N:3]=[C:4]([C:10]1([O:12][CH2:13][CH2:14][O:15]1)[CH3:11])[C:5]([OH:7])=[O:6]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 54382027Ethyl 2-methoxyimino-3,3-ethylenedioxybutyrate

Product 1

HCID 544524052-Methoxyimino-3,3-ethylenedioxybutyric acidYield 99.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a solution of ethyl 2-methoxyimino-3,3-ethylenedioxybutyrate (syn isomer, 180 g) in ethanol (1080 ml) was added 1N aqueous solution of sodium hydroxide (1600 ml) and the mixture was stirred for 2 hours and 10 minutes at ambient temperature. After the reaction mixture was adjusted to pH 7.3 with 6N hydrochloric acid, ethanol was distilled off under reduced pressure and when washed with diethyl ether (500 ml×2). To the resultant was added diethyl ether (1 l), adjusted to pH 1.5 with 6N hydrochloric acid and then diethyl ether layer was separated. The remaining aqueous layer was further extracted with diethyl ether (350 ml), and the remaining aqueous layer was adjusted to pH 1.3 with 6N hydrochloric acid and then further extracted with diethyl ether (350 ml×2). The diethyl ether layer and extracts were combined together, washed with a saturated aqueous solution of sodium chloride, dried over magnesium sulfate and then filtered. The filtrate was concentrated to give an oil (155.6 g) of 2-methoxyimino-3,3-ethylenedioxybutyric acid (syn isomer). (Yield: 99.3%)

Workup

  1. distillationwas distilled off under reduced pressure and when
  2. washwashed with diethyl ether (500 ml×2)
  3. additionTo the resultant was added diethyl ether (1 l)
  4. customdiethyl ether layer was separated
  5. extractionThe remaining aqueous layer was further extracted with diethyl ether (350 ml)
  6. extractionfurther extracted with diethyl ether (350 ml×2)
  7. washwashed with a saturated aqueous solution of sodium chloride
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered
  10. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-2b47407d85aa4fdc88faf83dd58496f7
Source dataset
uspto-grants-1986_06
Patent number
US04594446

Reaction notes

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