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

HRID 266425Notes

Reaction equation

HRID 266425 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-45171b0dda2042fc9239a40fa98d4291
Source dataset
uspto-grants-1997_07
Patent number
US05650539

Reaction notes

Loading…