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

HRID 1769416Notes

Reaction equation

HRID 1769416 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-dec80e2ef6024bea988e8a96e7156414
Source dataset
uspto-grants-1995_01
Patent number
US05380913

Reaction notes

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