Hydrochloric Acid → 4-Chloro-benzaldehyde oxime

HRID 600715Notes

Reaction equation

HRID 600715 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.Cl.[NH2:11][OH:12].N1C=CC=CC=1.Cl>C(Cl)Cl>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[N:11][OH:12])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 77264-ChlorobenzaldehydeHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 2191584-Chloro-benzaldehyde oxime

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Chlorobenzaldehyde (45.6 g; 0.325 mol), hydroxylamine hydrochloride (27.9 g; 0.401 mol) and pyridine (64 mL; 0.791 mol) in methylene chloride (600 mL) were stirred overnight at room temperature. The reaction mixture was poured into aqueous hydrochloric acid (2N; 300 mL) and extracted. The organic layer was washed with additional aqueous hydrochloric acid (2×300 mL), water (300 mL), dried (MgSO4), filtered and evaporated to yield oxime 1a as a white solid.

Workup

  1. extractionextracted
  2. washThe organic layer was washed with additional aqueous hydrochloric acid (2×300 mL), water (300 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-dec01e3068d14e62ad5b13417df02795
Source dataset
uspto-grants-2011_03
Patent number
US07902227B2

Reaction notes

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