Hydroxyamine hydrochloride → 4-(2-Chloroethyl)benzaldehyde oxime

HRID 2111012Notes

Reaction equation

HRID 2111012 reaction equation
[Cl:1][CH2:2][CH2:3][C:4]1[CH:11]=[CH:10][C:7]([CH:8]=O)=[CH:6][CH:5]=1.Cl.[NH2:13][OH:14]>C(O)C>[Cl:1][CH2:2][CH2:3][C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[N:13][OH:14])=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 152897604-(2-Chloroethyl)benzaldehyde

Product 1

HCID 860255684-(2-Chloroethyl)benzaldehyde oximeYield 95%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

4-(2-Chloroethyl)benzaldehyde (1.70 g, 10.08 mmol) was dissolved in ethanol (35 ml), hydroxylamine hydrochloride (1.05 g, 15.11 mmol) was added, and the mixture was stirred at 50° C. for 2 hours. Ethanol was evaporated under reduced pressure, and water was added. 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 (1.75 g, 95%).

Workup

  1. customEthanol was evaporated under reduced pressure, and 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-04e85a09515e474dbdfeafb3e266812d
Source dataset
uspto-grants-2009_04
Patent number
US07517996B2

Reaction notes

Loading…