Hydrochloric Acid → 4-Chloro-2',4'-dichlorobenzophenone oxime

HRID 47083Notes

Reaction equation

HRID 47083 reaction equation
[Cl:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][C:9]=2[Cl:15])=O)=[CH:4][CH:3]=1.Cl.[NH2:19][OH:20].[OH-].[K+].Cl>O.C(O)C>[Cl:1][C:2]1[CH:17]=[CH:16][C:5]([C:6](=[N:19][OH:20])[C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][C:9]=2[Cl:15])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 5874902,4,4'-Trichlorobenzophenone

Product 1

HCID 867367114-Chloro-2',4'-dichlorobenzophenone oximeYield 83.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

A mixture of 4-chloro 2',4'-dichlorobenzophenone (8 g.), hydroxylamine hydrochloride (2.9 g.), powdered potassium hydroxide (7.7 g.), ethanol (10 ml.) and water (2 ml.) was heated under reflux for 15 minutes. The mixture was poured into water (300 ml.) containing concentrated hydrochloric acid (30 ml.), and the precipitated oil was left to crystallise. The mixture was then filtered, and the solid residue (7.0 g., 83% yield) of 4-chloro-2',4'-dichlorobenzophenone oxime (m.p. 98°-100° C.) was used in the above process without further purification. A sample recrystallised from petrol also had m.p. 98°-100° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 15 minutes
  3. waitthe precipitated oil was left
  4. customto crystallise
  5. filtrationThe mixture was then filtered

Sources & evidence

ORD record
ord-819e2acfe2134004b7e694b3f9e9e0f8
Source dataset
uspto-grants-1979_11
Patent number
US04176194

Reaction notes

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