Ethanol → 4-Chloro-benzaldehyde oxime

HRID 1576972Notes

Reaction equation

HRID 1576972 reaction equation
Cl.[NH2:2][OH:3].[Cl:4][C:5]1[CH:12]=[CH:11][C:8]([CH:9]=O)=[CH:7][CH:6]=1.C(O)C>O.[OH-].[Na+]>[Cl:4][C:5]1[CH:12]=[CH:11][C:8]([CH:9]=[N:2][OH:3])=[CH:7][CH:6]=1

Participants

6

Reactant 3

HCID 702EthanolHCID 77264-ChlorobenzaldehydeHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 2191584-Chloro-benzaldehyde oximeYield 75.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 14798Sodium HydroxideSolvent

Procedure

To a solution of 50 g of hydroxylamine hydrochloride in 300 ml of water was added a suspension of 20 g of 4-chlorobenzaldehyde in 200 ml of 10% aqueous sodium hydroxide solution. Ethanol was then added until the mixture was clear. The solution was heated on a steam bath for 25 minutes, then cooled in an ice bath. The solid which separated was collected by filtration and dried in a vacuum desiccator. A second fraction was obtained by adding water just to the cloud point. This solid was collected and dried and the two products combined to give 16.75 g of 4-chlorobenzaldoxime, m.p. 108°-109°.

Workup

  1. temperatureThe solution was heated on a steam bath for 25 minutes
  2. temperaturecooled in an ice bath
  3. customThe solid which separated
  4. filtrationwas collected by filtration
  5. customdried in a vacuum desiccator
  6. customA second fraction was obtained
  7. customThis solid was collected
  8. customdried

Sources & evidence

ORD record
ord-4efdf72c83244bc9acdcee96e84e9e5f
Source dataset
uspto-grants-1976_09
Patent number
US03983246

Reaction notes

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