Methanol → 2-Phenoxybenzaldoxime

HRID 2081304Notes

Reaction equation

HRID 2081304 reaction equation
[O:1]([C:8]1[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=1[CH:10]=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO.Cl.[NH2:19][OH:20]>O>[O:1]([C:8]1[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=1[CH:10]=[N:19][OH:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 88060o-PhenoxybenzaldehydeHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 7374792-PhenoxybenzaldoximeYield 74.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

To 2-phenoxybenzaldehyde (4.96 g, 0.025 mole) were added anhydrous methanol (50 ml) and hydroxylamine hydrochloride (2.08 g, 0.03 mole), and the mixture was stirred at 60° C. for 3 hours. After completion of the reaction, water (200 ml) was added to the reaction mixture, which was extracted with methylene chloride and dried over magnesium sulfate. The crude product obtained by concentration under reduced pressure was purified by silica gel chromatography (ethyl acetate/n-hexane) to obtain 2-phenoxybenzaldoxime (3.95 g, yield: 74.1%) as a colorless oil.

Workup

  1. additionwas added to the reaction mixture, which
  2. extractionwas extracted with methylene chloride
  3. dry with materialdried over magnesium sulfate
  4. customThe crude product obtained by concentration under reduced pressure
  5. customwas purified by silica gel chromatography (ethyl acetate/n-hexane)

Sources & evidence

ORD record
ord-5de11ca1fd6b4e0fa024ed4d5d0ce3b4
Source dataset
uspto-grants-1993_02
Patent number
US05183921

Reaction notes

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