Hydrochloric Acid → 4'-Chloro-5-ethyl-2-hydroxybenzophenone-oxime

HRID 1606015Notes

Reaction equation

HRID 1606015 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[C:9]2[CH:14]=[C:13]([CH2:15][CH3:16])[CH:12]=[CH:11][C:10]=2[OH:17])=[CH:4][CH:3]=1.[OH-:19].[K+].Cl.[NH2:22]O.Cl>O.C(O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[N:22][OH:19])[C:9]2[CH:14]=[C:13]([CH2:15][CH3:16])[CH:12]=[CH:11][C:10]=2[OH:17])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 12562655(4-Chlorophenyl)(5-ethyl-2-hydroxyphenyl)methanone

Product 1

HCID 1362714664'-Chloro-5-ethyl-2-hydroxybenzophenone-oxime

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

4'-Chloro-5-ethyl-2-hydroxybenzophenone (65.2g) and potassium hydroxide (170g) in water (700ml) and ethanol (150ml.) were treated with hydroxylamine hydrochloride (70.0g), with cooling, and the resulting mixture was stirred for 18 hours at ambient temperature. Dissolution occurred during this time. The solution was acidified with 5N-hydrochloric acid and then extracted with ether (3×200ml.). The combined ether solutions were washed with 10% aqueous sodium carbonate solution (2×200ml) and evaporated to dryness to give an off-white solid. This solid was recrystallised from 40% benzene/60-80 petrol ether to give a white crystalline solid (29.9g), second crop (14.5g.) m.p.117°C.

Workup

  1. temperaturewith cooling
  2. dissolutionDissolution
  3. extractionextracted with ether (3×200ml.)
  4. washThe combined ether solutions were washed with 10% aqueous sodium carbonate solution (2×200ml)
  5. customevaporated to dryness
  6. customto give an off-white solid
  7. customThis solid was recrystallised from 40% benzene/60-80 petrol ether

Sources & evidence

ORD record
ord-5d1580e84227400f94e5fc33226cdb65
Source dataset
uspto-grants-1976_04
Patent number
US03951999

Reaction notes

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