Sodium Hydroxide → HCID 136205253, compound

HRID 2351175Notes

Reaction equation

HRID 2351175 reaction equation
[OH-].[Na+].[CH3:3][O:4][N:5]=[C:6]([C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[C:13]([N+:18]([O-:20])=[O:19])[CH:12]=1)[C:7]([O:9]C)=[O:8]>CO>[CH3:3][O:4][N:5]=[C:6]([C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[C:13]([N+:18]([O-:20])=[O:19])[CH:12]=1)[C:7]([OH:9])=[O:8]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 136210616HCID 136210616, compound

Product 1

HCID 136205253HCID 136205253, compoundYield 96.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 2N aqueous solution of sodium hydroxide (14 ml.) was added with stirring at ambient temperature to a solution of methyl 2-methoxyimino-2-(3-nitro-4-hydroxyphenyl)acetate (syn isomer) (3.5 g.) in methanol (70 ml.) and the mixture was stirred for 60 hours at ambient temperature. The reaction mixture was concentrated to dryness at 40° C. under reduced pressure and the residue was dissolved in water. The solution was washed with ethyl acetate, adjusted to pH 1 with 10% hydrochloric acid under ice-cooling and extracted with ethyl acetate. The extract was back-extracted with a saturated sodium bicarbonate aqueous solution. The aqueous extract was adjusted to pH 1 with conc. hydrochloric acid under ice-cooling and extracted with ethyl acetate. The extract was washed with ice-water and dried over magnesium sulfate. The solvent was concentrated to dryness at 40° C. under reduced pressure to give yellow crystals of 2-methoxyimino-2-(3-nitro-4-hydroxyphenyl)acetic acid (syn isomer) (3.2 g.), mp 142° to 143° C. (dec.).

Workup

  1. concentrationThe reaction mixture was concentrated to dryness at 40° C. under reduced pressure
  2. dissolutionthe residue was dissolved in water
  3. washThe solution was washed with ethyl acetate
  4. temperaturecooling
  5. extractionextracted with ethyl acetate
  6. extractionThe extract was back-extracted with a saturated sodium bicarbonate aqueous solution
  7. extractionThe aqueous extract
  8. temperaturecooling
  9. extractionextracted with ethyl acetate
  10. washThe extract was washed with ice-water
  11. dry with materialdried over magnesium sulfate
  12. concentrationThe solvent was concentrated to dryness at 40° C. under reduced pressure

Sources & evidence

ORD record
ord-99d8e258218a4f118ee676279a8c5579
Source dataset
uspto-grants-1989_10
Patent number
US04871860

Reaction notes

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