Sodium Hydroxide → Di-(4-chlorophenyl)methyleneamino-oxyacetic acid

HRID 47080Notes

Reaction equation

HRID 47080 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[N:16][O:17][CH2:18][C:19]([O:21]CC)=[O:20])[C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=2)=[CH:4][CH:3]=1.[OH-].[Na+]>C(O)C.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8](=[N:16][O:17][CH2:18][C:19]([OH:21])=[O:20])[C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 12942463Ethyl di-(4-chlorophenyl)methyleneamino-oxyacetate

Product 1

HCID 12942469Di-(4-chlorophenyl)methyleneamino-oxyacetic acidYield 33%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of ethyl di-(4-chlorophenyl)methyleneamino-oxyacetate (3.8 g.) in ethanol (140 ml.) and water (5 ml.) containing sodium hydroxide (5 g.) was heated under reflux for 16 hours. The mixture was then evaporated and the residue was diluted with water (100 ml.) and ether (50 ml.). The ether layer was separated and discarded. The aqueous layer was acidified to pH 2-3 by addition of 20% v/v hydrochloric acid and the solid (3.0 g.) which formed was separated and crystallised from ethyl acetate to give di-(4-chlorophenyl)methyleneamino-oxyacetic acid, m.p. 147°-148° C., in 33% yield.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 16 hours
  3. customThe mixture was then evaporated
  4. additionthe residue was diluted with water (100 ml.) and ether (50 ml.)
  5. customThe ether layer was separated
  6. additionThe aqueous layer was acidified to pH 2-3 by addition of 20% v/v hydrochloric acid
  7. customthe solid (3.0 g.) which formed
  8. customwas separated
  9. customcrystallised from ethyl acetate

Sources & evidence

ORD record
ord-ac95d6f815d148819b930d0e482c5f20
Source dataset
uspto-grants-1979_11
Patent number
US04176194

Reaction notes

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