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

HRID 2351187Notes

Reaction equation

HRID 2351187 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 an 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. extractionan extracted 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-02c215dc03614292bbfad1562884872b
Source dataset
uspto-grants-1989_10
Patent number
US04871860

Reaction notes

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