Sodium Hydroxide → 2-Methoxyimino-3,3-ethylenedioxy-4-chlorobutyric acid

HRID 463382Notes

Reaction equation

HRID 463382 reaction equation
[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]CC)=[O:6].[OH-].[Na+]>C(O)C>[CH3:1][O:2][N:3]=[C:4]([C:10]1([O:13][CH2:14][CH2:15][O:16]1)[CH2:11][Cl:12])[C:5]([OH:7])=[O:6]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 54025463Ethyl 2-methoxyimino-3,3-ethylenedioxy-4-chlorobutyrate

Product 1

HCID 544599112-Methoxyimino-3,3-ethylenedioxy-4-chlorobutyric acidYield 83.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl 2-methoxyimino-3,3-ethylenedioxy-4-chlorobutyrate (syn isomer, 7.3 g) in ethanol (35 ml) was added 1N aqueous solution of sodium hydroxide (35 ml) and the mixture was stirred for 2 hours at 40°-45° C. and then evaporated under reduced pressure. To the residue was added a saturated aqueous solution of sodium chloride (50 ml) and the mixture was washed with diethyl ether (60 ml). The aqueous layer was separated and then diethyl ether (100 ml) was added thereto. The mixture was adjusted to pH 1 with 10% hydrochloric acid, and the diethyl ether layer was separated and then the remaining aqueous layer was further extracted with diethyl ether (50 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 the solvent was distilled off. To the resultant oil was added benzene, and the benzene was distilled off. The resultant solid was washed in ligroin, collected by filtration and then dried to give 2-methoxyimino-3,3-ethylenedioxy-4-chlorobutyric acid (syn isomer, 5.4 g), mp 80°-81° C. (Yield: 83.3%).

Workup

  1. customevaporated under reduced pressure
  2. additionTo the residue was added a saturated aqueous solution of sodium chloride (50 ml)
  3. washthe mixture was washed with diethyl ether (60 ml)
  4. customThe aqueous layer was separated
  5. additiondiethyl ether (100 ml) was added
  6. customthe diethyl ether layer was separated
  7. extractionthe remaining aqueous layer was further extracted with diethyl ether (50 ml×2)
  8. washwashed with a saturated aqueous solution of sodium chloride
  9. dry with materialdried over magnesium sulfate
  10. distillationthe solvent was distilled off
  11. additionTo the resultant oil was added benzene
  12. distillationthe benzene was distilled off
  13. washThe resultant solid was washed in ligroin
  14. filtrationcollected by filtration
  15. customdried

Sources & evidence

ORD record
ord-b0c4a9bded334c98ba201be60b0eb5f2
Source dataset
uspto-grants-1985_05
Patent number
US04518774

Reaction notes

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