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

HRID 1689796

Reaction equation

HRID 1689796 reaction equation
[OH-:1].[Na+].Cl.[NH2:4]O.[Cl:6][C:7]1[CH:14]=[CH:13][CH:12]=[C:11]([Cl:15])[C:8]=1[CH:9]=O>O.C(O)C>[Cl:6][C:7]1[CH:14]=[CH:13][CH:12]=[C:11]([Cl:15])[C:8]=1[CH:9]=[N:4][OH:1]

Participants

6

Reactant 3

HCID 67372,6-DichlorobenzaldehydeHCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 91328Benzaldehyde, 2,6-dichloro-, oximeYield 99.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

Sodium hydroxide 3N (3.14 L, 9.43 mol) is added dropwise to a stirred suspension of hydroxylamine hydrochloride (675.55 g, 9.43 mol) in 0.5 L of water at 0° C. To this mixture is added dropwise a suspension of 2,6-dichlorobenzaldehyde (1500 g, 8.57 mol) in 7.5 L of ethanol and the reaction is heated at 90° C. overnight. The mixture is cooled to room temperature and then, concentrated to dryness. The solid is triturated in a mixture of H2O/EtOH, 10:1 (4.4 L), filtered and dried under high vacuum at 45° C. overnight. 1621.78 g of title compound (99% yield) is obtained as a white solid. MS (m/e): 190 (M+1)

Workup

  1. additionTo this mixture is added dropwise
  2. temperatureThe mixture is cooled to room temperature
  3. concentrationconcentrated to dryness
  4. customThe solid is triturated in a mixture of H2O/EtOH, 10:1 (4.4 L)
  5. filtrationfiltered
  6. customdried under high vacuum at 45° C. overnight

Sources & evidence

ORD record
ord-c3f0e80f6181496680572301a72f489f
Source dataset
uspto-grants-2012_04
Patent number
US08153624B2

Linked notes

Loading…