Water → 1-(2,4,6-Trichlorophenyl)-2-propanone O-methyloxime

HRID 2170299Notes

Reaction equation

HRID 2170299 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[C:4]([Cl:9])[C:3]=1[CH2:10][C:11](=O)[CH3:12].Cl.[CH3:15][O:16][NH2:17].O.[OH-].[Na+]>CO>[CH3:15][O:16][N:17]=[C:11]([CH3:12])[CH2:10][C:3]1[C:2]([Cl:1])=[CH:7][C:6]([Cl:8])=[CH:5][C:4]=1[Cl:9]

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium Hydroxide2×HCID 521874O-Methylhydroxylamine hydrochloride3×HCID 584436631-(2,4,6-Trichlorophenyl)-2-propanone

Product 1

HCID 767875151-(2,4,6-Trichlorophenyl)-2-propanone O-methyloxime

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

1-(2,4,6-trichloro-phenyl)-propan-2-one (273 g, 1.118 mol) was suspended in methanol (544 g) at ambient temperature. The resulting suspension was then heated under stirring to a temperature of 50° C. (most of the solid is dissolved). Then O-methyl-hydroxylamine hydrochloride as a 30% solution in water (358 g, 1.286 mol) was fed within 30-60 min. maintaining the temperature between 50-52° C. During the course of O-methyl-hydroxylamine hydrochloride addition the reaction mass turned into a two-phase system (liquid-liquid). At the end of O-methyl-hydroxylamine hydrochloride feed the pH was adjusted to 4-5 by slow addition of NaOH 30% (264 g 1.981 mol). The mixture was then stirred for 1-2 hours at 50-52° C. to allow the reaction to go to completion. Subsequently the pH was adjusted to 7-8 by adding NaOH 30% (8.5 g, 0.064 mol).

Workup

  1. temperatureThe resulting suspension was then heated
  2. dissolutionis dissolved)
  3. temperaturemaintaining the temperature between 50-52° C
  4. stirringThe mixture was then stirred for 1-2 hours at 50-52° C.
  5. customthe reaction

Sources & evidence

ORD record
ord-e686b82ee35946d98986024f722dbc6a
Source dataset
uspto-grants-2015_06
Patent number
US09051272B2

Reaction notes

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