Hydrochloric Acid → (2E)-2-hydroxyimino-2-(2-phenoxyphenyl)acetic acid

HRID 2081301Notes

Reaction equation

HRID 2081301 reaction equation
C[O:2][C:3](=[O:20])/[C:4](/[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[O:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[N:5]/[OH:6].CO.[OH-].[Na+].Cl>O>[OH:6]/[N:5]=[C:4](\[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[O:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)/[C:3]([OH:20])=[O:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 88276687methyl (2E)-2-hydroxyimino-2-(2-phenoxyphenyl)acetate

Product 1

HCID 88386642(2E)-2-hydroxyimino-2-(2-phenoxyphenyl)acetic acidYield 72.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To E-α-hydroxyimino-2-phenoxyphenylacetic acid methyl ester (9.99 g, 0.0368 mole) were added methanol (36.8 ml), sodium hydroxide (3.23 g, 0.081 mole) and water (36.8 ml) and the mixture was heated under reflux for one hour. After heating, conc. hydrochloric acid (1 ml) was added to the mixture under ice cooling and the precipitated crystals were filtered off and recrystallized (methanol/ethyl acetate/n-hexane) to obtain E-α-hydroxyimino-2-phenoxyphenylacetic acid (6.90 g, yield: 72.9%) as colorless crystals (decomposition: 180° C.).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for one hour
  3. temperatureAfter heating
  4. filtrationthe precipitated crystals were filtered off
  5. customrecrystallized (methanol/ethyl acetate/n-hexane)

Sources & evidence

ORD record
ord-a1b7b5e9a4864225b6dbcd57a86633ab
Source dataset
uspto-grants-1993_02
Patent number
US05183921

Reaction notes

Loading…