Potassium Hydroxide → Di-(4-methoxyphenyl)methyleneamino-oxyacetic acid

HRID 47082Notes

Reaction equation

HRID 47082 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=[N:18][O:19][CH2:20][C:21]([O:23]CC)=[O:22])[C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)=[CH:5][CH:4]=1.[OH-].[K+]>C(O)C.O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=[N:18][O:19][CH2:20][C:21]([OH:23])=[O:22])[C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 20385237Ethyl di-(4-methoxyphenyl)methyleneamino-oxyacetate

Product 1

HCID 12942475Di-(4-methoxyphenyl)methyleneamino-oxyacetic acidYield 55%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of ethyl di-(4-methoxyphenyl)methyleneamino-oxyacetate (1.0 g.) in ethanol (20 ml.) and water (5 ml.) containing potassium hydroxide (1.0 g.) was left at ambient temperature for 16 hours. The solution was evaporated and the residue partitioned between ether and water. The aqueous layer was separated and acidified with concentrated hydrochloric acid. The mixture was extracted with ether, the extract dried (MgSO4) and evaporated to give di-(4-methoxyphenyl)methyleneamino-oxyacetic acid as a solid (0.5 g.), m.p. 105°-107° C. (55% yield).

Workup

  1. customThe solution was evaporated
  2. customthe residue partitioned between ether and water
  3. customThe aqueous layer was separated
  4. extractionThe mixture was extracted with ether
  5. dry with materialthe extract dried (MgSO4)
  6. customevaporated

Sources & evidence

ORD record
ord-8dfd16dfa82e4d0dbd6eeb6d14cf08a0
Source dataset
uspto-grants-1979_11
Patent number
US04176194

Reaction notes

Loading…