Hydroxyamine hydrochloride → 3-Chloro-4-methylbenzaldoxime

HRID 1880232Notes

Reaction equation

HRID 1880232 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-methylbenzaldoxime

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 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 the resultant mixture was stirred at room temperature for 2 hours. After the completion of the reaction, the reaction mixture was diluted with 70 mL of ethyl acetate and the diluted reaction mixture was washed with water (30 mL×1) and then dehydrated and dried over saturated saline and anhydrous sodium sulfate in this order, followed by distilling off the solvent under reduced pressure to obtain 5.1 g of the objective substance as a white crystal. This crystal was used in the next process as it was without being further purified.

Workup

  1. customAfter the completion of the reaction
  2. customthe diluted reaction mixture
  3. washwas washed with water (30 mL×1)
  4. dry with materialdried over saturated saline and anhydrous sodium sulfate in this order
  5. distillationby distilling off the solvent under reduced pressure
  6. customto obtain 5.1 g of the objective substance as a white crystal

Sources & evidence

ORD record
ord-a1e18b6c285f4eaca6ba2e6163199e31
Source dataset
uspto-grants-2012_11
Patent number
US08318757B2

Reaction notes

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