Ethanol → N-[(3-phenoxyphenyl)methylidene]hydroxylamine

HRID 1659654

Reaction equation

HRID 1659654 reaction equation
[O:1]([C:8]1[CH:9]=[C:10]([CH:14]2OCCO2)[CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)C.[Cl-].[OH:23][NH3+:24].O>ClC(Cl)(Cl)Cl.C1C=CC=CC=1>[O:1]([C:8]1[CH:9]=[C:10]([CH:11]=[CH:12][CH:13]=1)[CH:14]=[N:24][OH:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 962WaterHCID 21645Hydroxylamine HClHCID 136438312-(3-Phenoxyphenyl)-1,3-dioxolane

Product 1

HCID 2393595N-[(3-phenoxyphenyl)methylidene]hydroxylamineYield 94%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of 24.2 g. of 2-(3-phenoxyphenyl)-1,3-dioxolane in 150 ml. of ethyl alcohol a solution of 14 g. of hydroxylammonium chloride in 150 ml. of water is added, and the mixture is boiled until no traces of starting compound can be detected by thin layer chromatography (silica gel, 1:1 mixture of benzene and tetrachloromethane, development: by UV light). Alcohol is distilled off and the aqueous residue is cooled in ice water. The precipitated crystals are filtered off. 20 g. (94%) of 3-phenoxybenzaldehyde oxime are obtained, melting at 45° to 46° C.

Workup

  1. distillationAlcohol is distilled off
  2. temperaturethe aqueous residue is cooled in ice water
  3. filtrationThe precipitated crystals are filtered off

Sources & evidence

ORD record
ord-35f5d7ec4b054a5cbd2d738578896b46
Source dataset
uspto-grants-1981_12
Patent number
US04304938

Linked notes

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