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

HRID 1955346Notes

Reaction equation

HRID 1955346 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([Cl:10])[C:3]=1[CH:4]=O.O1CCCC1.S([O-])([O-])(=O)=O.[OH:21][NH3+:22].O[NH3+].C(=O)(O)[O-].[Na+]>O>[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([Cl:10])[C:3]=1[CH:4]=[N:22][OH:21]

Participants

6

Reactant 4

HCID 67372,6-DichlorobenzaldehydeHCID 8028TetrahydrofuranHCID 24846Hydroxylamine sulfateHCID 516892Sodium Bicarbonate

Product 1

HCID 91328Benzaldehyde, 2,6-dichloro-, oxime

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

50.0 g (0.286 mol) of 2,6-dichlorobenzaldehyde were added to 250 ml of tetrahydrofuran and 250 ml of water, and 26.0 g (0.159 mol) of hydroxylammonium sulfate were added. The mixture was then stirred at 40° C. for 3 h, keeping the pH at 4-5 by adding sodium bicarbonate solution. The tetrahydrofuran was then distilled off under reduced pressure, and the residue was extracted with methyl tert-butyl ether, and the solution was dried over sodium sulfate and concentrated under reduced pressure. Yield 54.3 g (99.9%) of solid of melting point 150° C.

Workup

  1. additionwere added
  2. distillationThe tetrahydrofuran was then distilled off under reduced pressure
  3. extractionthe residue was extracted with methyl tert-butyl ether
  4. dry with materialthe solution was dried over sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1a3b095110fb461e8ec67b1e407e3846
Source dataset
uspto-grants-2000_09
Patent number
US06124469

Reaction notes

Loading…