Hydroxyamine hydrochloride → 4-{2-[4-(Hydroxyiminomethyl)phenoxy]ethyl}phenyl methanesulfonate

HRID 1595523Notes

Reaction equation

HRID 1595523 reaction equation
[CH3:1][S:2]([O:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH2:13][O:14][C:15]2[CH:20]=[CH:19][C:18]([CH:21]=O)=[CH:17][CH:16]=2)=[CH:8][CH:7]=1)(=[O:4])=[O:3].Cl.[NH2:24][OH:25].C([O-])(=O)C.[Na+]>C(O)C.O>[CH3:1][S:2]([O:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH2:13][O:14][C:15]2[CH:20]=[CH:19][C:18]([CH:21]=[N:24][OH:25])=[CH:17][CH:16]=2)=[CH:8][CH:7]=1)(=[O:4])=[O:3]

Participants

6

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 114159454-[2-(4-Formylphenoxy)ethyl]phenyl methanesulfonate

Product 1

HCID 867573774-{2-[4-(Hydroxyiminomethyl)phenoxy]ethyl}phenyl methanesulfonateYield 89.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

3.52 g (11 mmole) 4-[2-(4-formylphenoxy)ethyl]phenyl methanesulfonate was dissolved in 150 ml ethanol. 2.29 g (33 mmole) hydroxylamine hydrochloride and 3.6 g (44 mmole) sodium acetate in 30 ml water were added. The reaction mixture was stirred at 50° C. for 1 h 45 minutes. The solvent was evaporated in vacuo and water was added to give a white precipitate, which was filtered off and washed with hexane to give 3.3 g (yield 89%) of 4-{2-[4-(hydroxyiminomethyl)phenoxy]ethyl}phenyl methanesulfonate.

Workup

  1. customThe solvent was evaporated in vacuo and water
  2. additionwas added
  3. customto give a white precipitate, which
  4. filtrationwas filtered off
  5. washwashed with hexane

Sources & evidence

ORD record
ord-9affc54582d242db9ce484d4b49f2986
Source dataset
uspto-grants-2001_09
Patent number
US06288096B1

Reaction notes

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