4-(Chloromethyl)benzaldehyde → 4-Chloromethylbenzaldehyde oxime

HRID 2111001Notes

Reaction equation

HRID 2111001 reaction equation
[Cl:1][CH2:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[CH:5][CH:4]=1.Cl.[NH2:12][OH:13]>C(O)C>[Cl:1][CH2:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=[N:12][OH:13])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 3578774-(Chloromethyl)benzaldehydeHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 762257374-Chloromethylbenzaldehyde oximeYield 97%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

4-Chloromethylbenzaldehyde (11.93 g, 77.17 mmol) was dissolved in ethanol (200 ml), hydroxylamine hydrochloride (10.73 g, 154.41 mmol) was added, and the mixture was stirred at 50° C. for 3 hours. Ethanol was evaporated under reduced pressure, water was added, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to give the title compound (12.69 g, 97%).

Workup

  1. customEthanol was evaporated under reduced pressure, water
  2. additionwas added
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-bac323ceca1f4a00a7b0d4c70678c65c
Source dataset
uspto-grants-2009_04
Patent number
US07517996B2

Reaction notes

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