Hydroxylamine → Benzophenone oxime

HRID 2164713Notes

Reaction equation

HRID 2164713 reaction equation
[C:1]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:15][OH:16]>CO>[C:1](=[N:15][OH:16])([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 787HydroxylamineHCID 3102Benzophenone

Product 1

HCID 11324Benzophenone oxime

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
5 °C

Procedure

A 500 mL 3-neck flask was fitted with thermometer, dropping funnel and nitrogen blanket. Benzophenone (36.5 g; 0.2 mol) in absolute methanol (100 mL) was placed in the flask and cooled in an ice bath (5° C.) with stirring using a magnetic stirring bar. Hydroxylamine solution (133 mL) was slowly added and after completion of addition (15 minutes), the mixture was heated at reflux (65° C.). pH 8.6. After a total of 18 hours of heating under reflux, it was cooled and transferred to a 500 mL round bottom flask and concentrated on a rotovap. On cooling in ice bath, it was filtered and benzophenone oxime was collected as white crystalline solid (32.5 g; 89% yield). Purity, >97%.

Workup

  1. customA 500 mL 3-neck flask was fitted with thermometer
  2. additionafter completion of addition (15 minutes)
  3. temperaturethe mixture was heated
  4. temperatureat reflux (65° C.)
  5. temperatureAfter a total of 18 hours of heating
  6. temperatureunder reflux
  7. temperatureit was cooled
  8. customtransferred to a 500 mL round bottom flask
  9. concentrationconcentrated on a rotovap
  10. temperatureOn cooling in ice bath
  11. filtrationit was filtered
  12. custombenzophenone oxime was collected as white crystalline solid (32.5 g; 89% yield)

Sources & evidence

ORD record
ord-2ab1956fabdc4c969e2ac2e7834fb4f5
Source dataset
uspto-grants-1985_03
Patent number
US04507248

Reaction notes

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