4'-Chloro-2-hydroxy-4-methoxybenzophenone → 2-[(E)-C-(4-chlorophenyl)-N-hydroxycarbonimidoyl]-5-methoxyphenol

HRID 652949Notes

Reaction equation

HRID 652949 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][C:10]=2[OH:17])=[CH:4][CH:3]=1.Cl.[NH2:20][OH:21]>N1C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5](/[C:8](=[N:20]\[OH:21])/[C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][C:10]=2[OH:17])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 665574'-Chloro-2-hydroxy-4-methoxybenzophenoneHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 1364774242-[(E)-C-(4-chlorophenyl)-N-hydroxycarbonimidoyl]-5-methoxyphenol

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 382 g of 4'-chloro-2-hydroxy-4-methoxybenzophenone, 230 g hydroxylamine hydrochloride and 1.5 liters of pyridine is heated under reflux for 3 hr. The solvent is evaporated and the residue is partitioned between hydrochloric acid and ethyl acetate. The organic extracts are combined and washed with saturated sodium chloride solution. The solvent is removed to afford a mixture of E- and Z-oxime isomers which is separated on a Waters Prep IC System 500 using 5% ethyl acetate/toluene as the eluting system to afford E-4'-chloro-2-hydroxy-4-methoxybenzophenone oxime, mp 159° C.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 3 hr
  3. customThe solvent is evaporated
  4. customthe residue is partitioned between hydrochloric acid and ethyl acetate
  5. washwashed with saturated sodium chloride solution
  6. customThe solvent is removed
  7. customto afford
  8. customis separated on a Waters Prep IC System 500 using 5% ethyl acetate/toluene as the eluting system

Sources & evidence

ORD record
ord-7f4e40c9dec042a39ba93725c6bc7fca
Source dataset
uspto-grants-1987_06
Patent number
US04673746

Reaction notes

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