Hydrochloric Acid → 2-Ethoxyimino-2-(3-methoxyphenyl)acetic acid

HRID 261668Notes

Reaction equation

HRID 261668 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9](=O)[C:10]([OH:12])=[O:11])[CH:6]=[CH:7][CH:8]=1.C(=O)(O)[O-].[Na+].Cl.[CH2:20]([O:22][NH2:23])[CH3:21].Cl>O>[CH2:20]([O:22][N:23]=[C:9]([C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=1)[C:10]([OH:12])=[O:11])[CH3:21]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 76850O-ethylhydroxylamine hydrochlorideHCID 516892Sodium Bicarbonate3×HCID 12613727(3-Methoxyphenyl)glyoxylic acid

Product 1

HCID 539416962-Ethoxyimino-2-(3-methoxyphenyl)acetic acidYield 98.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 2-(3-methoxyphenyl)glyoxylic acid (1.8 g.) in an aqueous solution of sodium bicarbonate was adjusted to pH 7.0. On the other hand, a solution of O-ethylhydroxylamine hydrochloride (1.4 g.) in water (20 ml.) was adjusted to pH 7.0 with sodium bicarbonate. Two solutions were combined together, adjusted to pH 5.5 with 10% hydrochloric acid and stirred overnight at ambient temperature. The reaction mixture was adjusted to pH 7.5 with sodium bicarbonate and washed with ethyl acetate. The aqueous layer was adjusted to pH 1.0 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 distilled off under reduced pressure to give oil of 2-ethoxyimino-2-(3-methoxyphenyl)acetic acid (syn isomer) (2.2 g.).

Workup

  1. washwashed with ethyl acetate
  2. temperaturecooling
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with ice-water
  5. dry with materialdried over magnesium sulfate
  6. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-ba1c27e46bdd4904aa785771aadba275
Source dataset
uspto-grants-1979_08
Patent number
US04166115

Reaction notes

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