Hydroxyamine hydrochloride → 1-(2-Chlorophenoxy)-2-propanone oxime

HRID 22921Notes

Reaction equation

HRID 22921 reaction equation
[Cl:1][C:2]1[CH:12]=[CH:11][CH:10]=[CH:9][C:3]=1[O:4][CH2:5][C:6]([CH3:8])=O.Cl.[NH2:14][OH:15]>[OH-].[Na+].C(O)C>[Cl:1][C:2]1[CH:12]=[CH:11][CH:10]=[CH:9][C:3]=1[O:4][CH2:5][C:6](=[N:14][OH:15])[CH3:8]

Participants

5

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 11229185(2-Chloro-phenoxy)-acetone

Product 1

HCID 725218331-(2-Chlorophenoxy)-2-propanone oximeYield 3.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

1-(2-Chlorophenoxy)acetone (106.6 g, 0.58 mol) (J. Am. Chem. Soc., 75, 1953, 1134) was added to a solution of hydroxylamine hydrochloride (27.8 g, 4 mol) in 2N sodium hydroxide solution (420 ml) and sufficient ethanol to give a clear solution. The reaction mixture was refluxed for 30 minutes then concentrated in vacuo, the crude residue was extracted with diethyl ether (3×200 ml). The combined organic layers were dried over magnesium sulphate and concentrated in vacuo. The residue was distilled to give the title product (134-136° C./1.35 mmHg) (4.5 g, 3.9%); 1H NMR (CDCl3 400 MHz) δ: 2.05 (s, 3H), 5.00 (s, 2H), 6.90-7.00 (m, 2H), 7.10 (t, 1H), 7.30 (d, 1H), 7.60 (s, 1H). Anal. Found C, 54.95; H, 5.05. C9H10NO2Cl requires C, 54.15; H, 5.05%.

Workup

  1. customto give a clear solution
  2. temperatureThe reaction mixture was refluxed for 30 minutes
  3. concentrationthen concentrated in vacuo
  4. extractionthe crude residue was extracted with diethyl ether (3×200 ml)
  5. dry with materialThe combined organic layers were dried over magnesium sulphate
  6. concentrationconcentrated in vacuo
  7. distillationThe residue was distilled

Sources & evidence

ORD record
ord-f34e02177f3d48c49d62ad3e302dc6bb
Source dataset
uspto-grants-2005_02
Patent number
US06849649B2

Reaction notes

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