Reaction #75358

Reaction equation

ethyl di-(4-chlorophenyl)methyleneamino-oxyacetate

sodium hydroxide

→

di-(4-chlorophenyl)methyleneamino-oxyacetic acid

Yield 33.0%

Solvents

ethanol

water

Conditions

Workup

1. 1
   Temperaturewas heated
2. 2
   Temperatureunder reflux for 16 hours
3. 3
   OtherThe mixture was then evaporated
4. 4
   workup.ADDITIONthe residue was diluted with water (100 ml.) and ether (50 ml.)
5. 5
   OtherThe ether layer was separated
6. 6
   workup.ADDITIONThe aqueous layer was acidified to pH 2-3 by addition of 20% v/v hydrochloric acid
7. 7
   Otherthe solid (3.0 g.) which formed
8. 8
   Otherwas separated
9. 9
   Othercrystallised from ethyl acetate

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.

Source