Sulfuric Acid → 2-Methoxyimino-3,3-ethylenedioxy-4-bromobutyric acid

HRID 1982016Notes

Reaction equation

HRID 1982016 reaction equation
[OH-].[Na+].[CH3:3][O:4][N:5]=[C:6]([C:12]1([O:18][CH2:17][CH2:16][O:15]1)[CH2:13][Br:14])[C:7]([O:9]CC)=[O:8].S(=O)(=O)(O)O>O.CO>[CH3:3][O:4][N:5]=[C:6]([C:12]1([O:15][CH2:16][CH2:17][O:18]1)[CH2:13][Br:14])[C:7]([OH:9])=[O:8]

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 53760491Ethyl 2-methoxyimino-3,3-ethylenedioxy-4-bromobutyrate

Product 1

HCID 536757272-Methoxyimino-3,3-ethylenedioxy-4-bromobutyric acidYield 74.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

A solution of sodium hydroxide (8.64 g) in water (20 ml) was added to a solution of ethyl 2-methoxyimino-3,3-ethylenedioxy-4-bromobutyrate (syn isomer, 26.6 g) in methanol (60 ml) under ice-cooling, stirred at ambient temperature for 2 hours. Water (100 ml) was added to the resultant solution and adjusted to pH 7.0 with 20% sulfuric acid under ice-cooling. After removing methanol therefrom in vacuo, the solution was washed with diethyl ether (100 ml). Diethyl ether (100 ml) was added to the aqueous layer and adjusted to pH 2.0 with 20% sulfuric acid below 10° C. The organic layer was separated, and then the aqueous layer was extracted with diethyl ether (100 ml) twice. The organic layer was washed with water and a sodium chloride saturated aqueous solution in turn, and dried over magnesium sulfate. The solution was concentrated in vacuo and the residue was allowed to stand in refrigerator overnight to give 2-methoxyimino-3,3-ethylenedioxy-4-bromobutyric acid (syn isomer, 18.0 g.). (Yield: 74.7%).

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. customAfter removing methanol
  4. washin vacuo, the solution was washed with diethyl ether (100 ml)
  5. additionDiethyl ether (100 ml) was added to the aqueous layer and adjusted to pH 2.0 with 20% sulfuric acid below 10° C
  6. customThe organic layer was separated
  7. extractionthe aqueous layer was extracted with diethyl ether (100 ml) twice
  8. washThe organic layer was washed with water
  9. dry with materiala sodium chloride saturated aqueous solution in turn, and dried over magnesium sulfate
  10. concentrationThe solution was concentrated in vacuo
  11. customto stand in refrigerator overnight

Sources & evidence

ORD record
ord-26163d9e55da4c9990ae73b176781baf
Source dataset
uspto-grants-1986_06
Patent number
US04594446

Reaction notes

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