Ethanol → 2,3,6-Trichlorobenzylideneaminooxyacetic Acid

HRID 905368Notes

Reaction equation

HRID 905368 reaction equation
Cl[C:2]1[C:9]([Cl:10])=[CH:8][CH:7]=[C:6]([Cl:11])[C:3]=1[CH:4]=O.C(O)C.[ClH:15].[C:16]([CH2:19][O:20][NH2:21])([OH:18])=[O:17].C(CON)(O)=O.C([O-])(=O)C.[Na+]>O>[Cl:15][CH:19]([O:20][N:21]=[CH:4][C:3]1[C:6]([Cl:11])=[CH:7][CH:8]=[C:9]([Cl:10])[CH:2]=1)[C:16]([OH:18])=[O:17]

Participants

6

Reactant 4

HCID 702EthanolHCID 207812,3,6-TrichlorobenzaldehydeHCID 517045Sodium AcetateHCID 2723609Aminooxyacetic acid hemihydrochloride

Product 1

HCID 1317133272,3,6-Trichlorobenzylideneaminooxyacetic Acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A warm solution of 3.0 gm. (0.014 mole) of 2,3,6-trichlorobenzaldehyde in 50 ml. of ethanol was stirred into a warm solution of 1.6 gm. (0.015 equiv.) of carboxymethoxylamine hemihydrochloride and 0.7 gm. (0.008 mole) of anhyd. sodium acetate in 50 ml. water. Heating on the steam bath was maintained for one-half hour: then the reaction mixture was evaporated by 3/4 volume and was cooled. The solid present was removed by filtration, washed with water and dried in vacuum dessicator over phosphorus pentoxide to obtain 3.9 gm. (96.5%) of crude product melting at 159°-160° C. This material, twice recrystallized from aqueous-isopropyl alcohol, melted at 160°-161° C.

Workup

  1. temperatureHeating on the steam bath
  2. temperaturewas maintained for one-half hour
  3. customthe reaction mixture was evaporated by 3/4 volume
  4. temperaturewas cooled
  5. customThe solid present was removed by filtration
  6. washwashed with water
  7. dry with materialdried in vacuum dessicator over phosphorus pentoxide
  8. customto obtain 3.9 gm
  9. customThis material, twice recrystallized from aqueous-isopropyl alcohol, melted at 160°-161° C.

Sources & evidence

ORD record
ord-5e8111f1141546d2afe8d8ea6c8beaef
Source dataset
uspto-grants-1983_12
Patent number
US04423241

Reaction notes

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