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

HRID 1897111Notes

Reaction equation

HRID 1897111 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-c6dc8ae9158f43109baa727df2eef927
Source dataset
uspto-grants-2013_08
Patent number
US08518974B2

Reaction notes

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