Sodium Carbonate → N-[2-(4-Fluorophenyl)ethylidene]hydroxylamine

HRID 1608263Notes

Reaction equation

HRID 1608263 reaction equation
[Cl-].[OH:2][NH3+:3].[F:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH:12]=O)=[CH:7][CH:6]=1.C(=O)([O-])[O-].[Na+].[Na+]>O.C(Cl)Cl>[F:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH:12]=[N:3][OH:2])=[CH:7][CH:6]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 21645Hydroxylamine HClHCID 111263222-(4-Fluorophenyl)acetaldehyde

Product 1

HCID 57348170N-[2-(4-Fluorophenyl)ethylidene]hydroxylamineYield 90.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent

Procedure

113 g of hydroxylammonium chloride in 300 ml of water are added to 160 g of p-fluorophenylacetaldehyde in 500 ml of methylene chloride. A solution of 87 g of sodium carbonate in 300 ml of water is slowly added dropwise to the stirred mixture at room temperature, and the reaction is allowed to continue for 2 days. The organic phase is separated off, washed with water, dried over Na2SO4 and filtered, and the filtrate is freed from the solvent. 161 g of p-fluorophenylacetaldoxime of melting point 113°-115° C. are obtained. 200 MHz NMR spectrum in CDCl3 : ##STR10## (cis/trans isomer mixture=1:1)

Workup

  1. customThe organic phase is separated off
  2. washwashed with water
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered

Sources & evidence

ORD record
ord-061f32367c4040ff8c4bb71241e3e591
Source dataset
uspto-grants-1989_09
Patent number
US04870100

Reaction notes

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