Water → o-Chlorobenzaldoxime

HRID 2407655Notes

Reaction equation

HRID 2407655 reaction equation
Cl.[NH2:2][OH:3].[Cl:4][C:5]1[CH:12]=[CH:11][CH:10]=[CH:9][C:6]=1[CH:7]=O.C(=O)([O-])[O-].[Na+].[Na+].O>CO>[Cl:4][C:5]1[CH:12]=[CH:11][CH:10]=[CH:9][C:6]=1[CH:7]=[N:2][OH:3]

Participants

6

Reactant 4

HCID 962WaterHCID 69962-ChlorobenzaldehydeHCID 10340Sodium CarbonateHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 96239o-ChlorobenzaldoximeYield 98.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Hydroxylamine hydrochloride (35.6 g) was added to a 0° C. mixture of 2-chlorobenzaldehyde (60.0 g) and sodium carbonate (22.6 g) in methanol (1.0 L)-water (1.0 L). The reaction was stirred overnight and then concentrated to half volume. The mixture was extracted twice with ethyl acetate. The organics were combined, washed with brine, dried over anhydrous magnesium sulfate and concentrated to obtain the title compound (65.4 g) having the following physical data.

Workup

  1. concentrationconcentrated to half volume
  2. extractionThe mixture was extracted twice with ethyl acetate
  3. washwashed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-3f202e26b20f4b8ba44a729a6853c83c
Source dataset
uspto-grants-2014_08
Patent number
US08809538B2

Reaction notes

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