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

HRID 328655Notes

Reaction equation

HRID 328655 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-1687a6d7eb474183bd1cc4f427b1f65c
Source dataset
uspto-grants-1977_04
Patent number
US04018645

Reaction notes

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