3-Chlorobenzaldehyde → Benzaldehyde, m-chloro-, oxime, (Z)-

HRID 331813Notes

Reaction equation

HRID 331813 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=O.Cl.[NH2:11][OH:12].C([O-])(=O)C.[Na+]>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)/[CH:5]=[N:11]\[OH:12]

Participants

5

Reactant 3

HCID 114773-ChlorobenzaldehydeHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium Acetate

Product 1

HCID 5372364Benzaldehyde, m-chloro-, oxime, (Z)-Yield 98%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 3-chlorobenzaldehyde (50 g, 355 mmol) and hydroxylamine hydrochloride (38 g, 543 mmol) in ethanol (200 mL) containing sodium acetate (46 g, 558 mmol) was heated under reflux for 3 h. After 30 min stirring at room temperature a white solid precipitated and the resulting mixture was then diluted with water and acidified with HCl (4 N). The white precipitate was then filtered off, washed with water and dried under high vacuum to afford the title compound (54 g, 98%) which was obtained as a white solid. Mp: 64-66° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 3 h
  3. customprecipitated
  4. additionthe resulting mixture was then diluted with water
  5. filtrationThe white precipitate was then filtered off
  6. washwashed with water
  7. customdried under high vacuum

Sources & evidence

ORD record
ord-df067ac24d3645e99b54c30482841de7
Source dataset
uspto-grants-2014_11
Patent number
US08877782B2

Reaction notes

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