Ethyl Salicylate → Salicylhydroxamic Acid

HRID 1791940Notes

Reaction equation

HRID 1791940 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-4f3cc27de9b54598aeb7b5073ac9d63b
Source dataset
uspto-grants-2006_07
Patent number
US07074794B2

Reaction notes

Loading…