Sulfuric Acid → Acetophenonoxime

HRID 2164715Notes

Reaction equation

HRID 2164715 reaction equation
S(O)(O)(=O)=O.[NH2:6][OH:7].[OH-].[Na+].[C:10]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)(=O)[CH3:11].OS(O)(=O)=O>CO>[C:10](=[N:6][OH:7])([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH3:11]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 7410AcetophenoneHCID 14798Sodium HydroxideHCID 159255Hydroxylamine, sulfate (1:1)

Product 1

HCID 69185Acetophenonoxime

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent3×

Conditions

Temperature
40 °C

Procedure

In a 500 mL 3-neck flask was placed solid hydroxylamine sulfate (28 g; 0.17 mol) and absolute methanol (100 mL) was added to it. The slurry was stirred vigorously using a magnetic bar over a stir plate and a solution of sodium hydroxide pellets (14 g; 0.35 mol) in absolute methanol (175 mL) was then added slowing with cooling in ice bath (<5° C.). At the completion of addition of the solution, acetophenone (40 g; 0.33 mol) was added and stirring in the cold was continued for 5 hours. Concentrated H2SO4 (1.8 g) was added to adjust the pH of the solution to 6.5. Methanol (50 mL) was added to the slurry and the mixture heated (40° C.) for 2 hours and then filtered hot. The clear filtrate (colorless) was concentrated under reduced pressure and crystalline acetophenone oxime was collected after cooling and filtration. Yield, 40.5 g (90.8%). Purity >98% of isomeric mixture.

Workup

  1. customIn a 500 mL 3-neck flask was placed
  2. temperaturewith cooling in ice bath (<5° C.)
  3. additionwas added
  4. stirringstirring in the cold
  5. filtrationfiltered hot
  6. concentrationThe clear filtrate (colorless) was concentrated under reduced pressure and crystalline acetophenone oxime
  7. customwas collected
  8. temperatureafter cooling
  9. filtrationfiltration
  10. customYield

Sources & evidence

ORD record
ord-5328bcdb67d24d7e950c3cf2df52adad
Source dataset
uspto-grants-1985_03
Patent number
US04507248

Reaction notes

Loading…