Acetic Anhydride → alpha-Chloro-O-Acetyl-4-Chlorobenzaldoxime

HRID 917986Notes

Reaction equation

HRID 917986 reaction equation
[Cl:1][C:2](=[N:10][OH:11])[C:3]1[CH:8]=[CH:7][C:6]([Cl:9])=[CH:5][CH:4]=1.[C:12](OC(=O)C)(=[O:14])[CH3:13]>O>[Cl:1][C:2](=[N:10][O:11][C:12](=[O:14])[CH3:13])[C:3]1[CH:4]=[CH:5][C:6]([Cl:9])=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 27555434-chloro-N-hydroxybenzene-1-carbonimidoyl chloride

Product 1

HCID 54422657alpha-Chloro-O-Acetyl-4-ChlorobenzaldoximeYield 77.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 19 g (0.1 mol) of α-chloro-4-chlorobenzaldoxime prepared above was added 20.6 g (2.0 mol) of acetic anhydride followed by heating on a water bath at a temperature of from 80° to 90°C for about 2 hours. After completion of the reaction, the reaction mixture was poured into water to give pale yellow crystals. The product thus obtained was filtered, dried and recrystallized from ligroin to give 18 g of the desired product as white crystals having a melting point of 76°-77°C. Yield, 77%.

Workup

  1. temperatureby heating on a water bath at a temperature of from 80° to 90°C for about 2 hours
  2. customAfter completion of the reaction
  3. customto give pale yellow crystals
  4. customThe product thus obtained
  5. filtrationwas filtered
  6. customdried
  7. customrecrystallized from ligroin

Sources & evidence

ORD record
ord-91285eff4b9040c58d4a02eff6af8657
Source dataset
uspto-grants-1976_07
Patent number
US03968240

Reaction notes

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