Hydroxyamine hydrochloride → 3-Chloro-4-methylbenzaldoxime

HRID 885797Notes

Reaction equation

HRID 885797 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[CH3:10])[CH:5]=O.Cl.[NH2:12][OH:13]>CO.O.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[CH3:10])[CH:5]=[N:12][OH:13]

Participants

6

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 124230853-Chloro-4-methylbenzaldehyde

Product 1

HCID 730143123-Chloro-4-methylbenzaldoximeYield 93%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

In a solution of 5.0 g of 3-chloro-4-methylbenzaldehyde in 40 mL of methanol and 30 mL of water, 4.7 g of hydroxylamine hydrochloride was added, and stirred at room temperature for 2 hours. After the completion of the reaction, the reaction mixture was diluted with 70 mL of ethyl acetate, washed with water (30 mL×1), and then dehydrated with and dried over saturated sodium chloride and anhydrous sodium sulfate in that order, and the solvent was distilled off under reduced pressure to obtain 5.1 g of the aimed product as white crystal. The resulting product was used as such without purification for the next step.

Workup

  1. customAfter the completion of the reaction
  2. washwashed with water (30 mL×1)
  3. dry with materialdried over saturated sodium chloride and anhydrous sodium sulfate in that order
  4. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-1e51d8a40c4e4bdcbe12010c8153493a
Source dataset
uspto-grants-2012_08
Patent number
US08242283B2

Reaction notes

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