Benzaldehyde → Syn-benzaldehyde oxime

HRID 868922

Reaction equation

HRID 868922 reaction equation
[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:9][OH:10].Cl.[OH-].[Na+]>C(O)C.O>[CH:1](=[N:9]/[OH:10])/[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 240BenzaldehydeHCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 5324470Syn-benzaldehyde oxime

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a stirred solution of benzaldehyde (3 g, 28.3 mmol) in ethanol (50 mL) and water (30 mL), NH2OH hydrochloride (3.9 g, 56.6 mmol) and sodium hydroxide (2.26 g, 56.6 mmol) were added. The mixture was heated at reflux for 6 hours. The resulting mixture was cooled to room temperature and extracted with EtOAc, and the organic layer was dried over anhydrous sodium sulfate. The solution was then concentrated under vacuum to give the title compound as an oil-like solid (3.4 g), which was used in the next step without further purification. MS (ESI) m/z 121 (M+H+).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 6 hours
  3. extractionextracted with EtOAc
  4. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  5. concentrationThe solution was then concentrated under vacuum

Sources & evidence

ORD record
ord-f19df7ebeba944b88fc980f07852d648
Source dataset
uspto-grants-2015_03
Patent number
US08969349B2

Linked notes

Loading…