Ethyl Salicylate → Salicylhydroxamic Acid

HRID 1829149Notes

Reaction equation

HRID 1829149 reaction equation
Cl.[OH:2][NH3+:3].[C:4]([O:13]CC)(=O)[C:5]1[C:6](=[CH:8][CH:9]=[CH:10][CH:11]=1)[OH:7]>[OH-].[Na+].O1CCOCC1>[C:4]([NH:3][OH:2])(=[O:13])[C:5]1[C:6](=[CH:8][CH:9]=[CH:10][CH:11]=1)[OH:7]

Participants

5

Reactant 2

HCID 8365Ethyl SalicylateHCID 22029257Hydroxyammonium hydrochloride

Product 1

HCID 66644Salicylhydroxamic AcidYield 54.3%

Reagents, catalysts & solvents 2

HCID 14798Sodium HydroxideSolventHCID 312751,4-DioxaneSolvent

Procedure

Hydroxylammonium hydrochloride (15 g) was dissolved in 10% aqueous sodium hydroxide solution (220 mL), and a solution of ethyl salicylate (24 g) in 1,4-dioxane (70 mL) was gradually added, and the mixture was stirred at room temperature for 5 hr. The reaction mixture was concentrated until the amount thereof became almost the half, and acidified with conc. hydrochloric acid. The precipitated solid was collected by filtration, which was then recrystallized from methanol to give salicylhydroxamic acid (12 g) as white crystals.

Workup

  1. concentrationThe reaction mixture was concentrated until the amount
  2. filtrationThe precipitated solid was collected by filtration, which
  3. customwas then recrystallized from methanol

Sources & evidence

ORD record
ord-c8d23df14f1c48c3918cfeef72b38853
Source dataset
uspto-grants-2006_06
Patent number
US07060722B2

Reaction notes

Loading…