Sodium Hydroxide → HCID 22915488, compound

HRID 1377923Notes

Reaction equation

HRID 1377923 reaction equation
[I:1][C:2]1[CH:15]=[CH:14][C:5]([O:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]([OH:13])=O)=[CH:4][CH:3]=1.S(Cl)(Cl)=O.[OH-].[Na+].Cl.[C:23]([O:27][NH2:28])([CH3:26])([CH3:25])[CH3:24].[NH4+].[Cl-]>C(OCC)(=O)C>[C:23]([O:27][NH:28][C:11](=[O:13])[CH2:10][CH2:9][CH2:8][CH2:7][O:6][C:5]1[CH:4]=[CH:3][C:2]([I:1])=[CH:15][CH:14]=1)([CH3:26])([CH3:25])[CH3:24]

Participants

7

Reactant 5

HCID 14798Sodium HydroxideHCID 24386Thionyl ChlorideHCID 25517Ammonium ChlorideHCID 2777906O-tert-butylhydroxylamine hydrochlorideHCID 22915460HCID 22915460, compound

Product 1

HCID 22915488HCID 22915488, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 5-(4-iodophenoxy)pentanoic acid (6.00 g, 18.8 mmol) and excess thionyl chloride was heated at reflux for 30 minutes. The reaction mixture was cooled to ambient temperature and concentrated in vacuo. The residue was azeotroped three times with ethyl ether and then was taken up in THF. To the acid chloride solution was added an aqueous solution of O-tert-butylhydroxylamine (24 mmol; prepared by adding aqueous 3M NaOH to an aqueous solution of O-tert-butylhydroxylamine hydrochloride) and the cloudy solution was stirred for 20 hours. The reaction mixture was poured into a mixture of ethyl acetate and saturated aqueous NH4Cl. The organic phase was washed with water and brine, dried over MgSO4, filtered, and concentrated in vacuo to give O-tert-butyl 5-(4-iodophenoxy)pentanohydroxamic acid (6.52 g).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 30 minutes
  3. concentrationconcentrated in vacuo
  4. customThe residue was azeotroped three times with ethyl ether
  5. additionTo the acid chloride solution was added an aqueous solution of O-tert-butylhydroxylamine (24 mmol
  6. customprepared
  7. washThe organic phase was washed with water and brine
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-181f59e616a147eca82fc6709e26c3e8
Source dataset
uspto-grants-1997_09
Patent number
US05665777

Reaction notes

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