Ethanol → 3-(4-Methoxyphenoxy)benzaldehyde oxime

HRID 449512Notes

Reaction equation

HRID 449512 reaction equation
[CH3:1][O:2][C:3]1[CH:17]=[CH:16][C:6]([O:7][C:8]2[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=2)[CH:11]=O)=[CH:5][CH:4]=1.C(O)C.Cl.[NH2:22][OH:23].C([O-])(=O)C.[Na+]>O>[CH3:1][O:2][C:3]1[CH:17]=[CH:16][C:6]([O:7][C:8]2[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=2)[CH:11]=[N:22][OH:23])=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 1235533-(4-Methoxyphenoxy)benzaldehydeHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium Acetate

Product 1

HCID 723078873-(4-Methoxyphenoxy)benzaldehyde oximeYield 102.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
85 °C

Procedure

3-(4-Methoxyphenoxy)benzaldehyde (Aldrich, Cat. #195898) (0.10 g, 0.44 mmol) was dissolved in ethanol (2.1 mL, 37 mmol) and water (0.43 mL) at r.t., and the hydroxylamine hydrochloride (0.061 g, 0.88 mmol) and sodium acetate (0.072 g, 0.88 mmol) were added. The reaction was heated in a sealed tube to 85° C. for 2 h., and allowed to cool to r.t. The mixture was partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over magnesium sulfate and concentrated under reduced pressure to give 3-(4-methoxyphenoxy)benzaldehyde oxime (0.11 g, 100%) as an oily residue.

Workup

  1. temperatureto cool to r.t
  2. customThe mixture was partitioned between ethyl acetate and water
  3. washThe organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b7c796058b6d4143bdff600903557c31
Source dataset
uspto-grants-2013_07
Patent number
US08481732B2

Reaction notes

Loading…