Water → Benzaldehyde, 2,6-dichloro-, oxime

HRID 1689797

Reaction equation

HRID 1689797 reaction equation
C(N(CC)CC)C.[Cl:8][C:9]1[CH:16]=[CH:15][CH:14]=[C:13]([Cl:17])[C:10]=1[CH:11]=O.Cl.[NH2:19][OH:20].O>ClCCl>[Cl:8][C:9]1[CH:16]=[CH:15][CH:14]=[C:13]([Cl:17])[C:10]=1[CH:11]=[N:19][OH:20]

Participants

6

Reactant 4

HCID 962WaterHCID 67372,6-DichlorobenzaldehydeHCID 8471TriethylamineHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 91328Benzaldehyde, 2,6-dichloro-, oximeYield 132.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Alternate procedure: Add triethylamine (23.1 g, 229 mmol) dropwise to a solution of 2,6-dichloro-benzaldehyde (20.0 g, 114 mmol) and hydroxylamine hydrochloride (10.3 g, 149 mmol) in dichloromethane (200 mL). Stir the reaction mixture for 8 h. Add water (200 mL). Separate the phases and extract the aqueous phase with dichloromethane (100 mL). Wash the combined organic phases with water (100 mL). Concentrate the combined organic phases to provide 28.8 g (94%) of the title compound.

Workup

  1. customSeparate the phases
  2. extractionextract the aqueous phase with dichloromethane (100 mL)
  3. washWash the combined organic phases with water (100 mL)
  4. concentrationConcentrate the combined organic phases

Sources & evidence

ORD record
ord-868f23b784d94cea9d97e1fd57aa73cf
Source dataset
uspto-grants-2012_04
Patent number
US08153624B2

Linked notes

Loading…