Sodium Hydroxide → HCID 22915485, compound

HRID 1377916Notes

Reaction equation

HRID 1377916 reaction equation
[C:1]1([C:7]2[CH:8]=[C:9]([CH:16]=[CH:17][CH:18]=2)[O:10][CH2:11][CH2:12][C:13](O)=[O:14])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(Cl)(Cl)=O.[OH-:23].[Na+].Cl.[NH2:26]O>O>[C:1]1([C:7]2[CH:8]=[C:9]([CH:16]=[CH:17][CH:18]=2)[O:10][CH2:11][CH2:12][C:13]([NH:26][OH:23])=[O:14])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 24386Thionyl ChlorideHCID 443297Hydroxyamine hydrochlorideHCID 22915468HCID 22915468, compound

Product 1

HCID 22915485HCID 22915485, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3-(3-phenylphenoxy)propionic acid (0.27 g, 1.1 mmol) and excess thionyl chloride was heated at reflux for 30 minutes. The 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 (30 mL). To the acid chloride solution was added aqueous hydroxylamine (3.34 mmol; prepared by adding 2.8 mL of aqueous 50% NaOH to a solution in 5 mL water of hydroxylamine hydrochloride) and the reaction mixture was stirred for 4 hours. The reaction mixture was quenched with 1:1 dichloromethane-saturated aqueous NH4Cl. The aqueous phase was washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. The residue was taken up in ethyl ether and left standing at -30° C. for 3 days. The resulting crystals were collected to give 3-(3-phenylphenoxy)propanohydroxamic acid. mp 113°-116° C. 1H NMR (DMSO-d6) δ 10.58 (s, 1H), 8.68-8.63 (d, 1H, J=1.5 Hz), 7.67-7.65 (d, 2H, J=7 Hz), 7.48-7.43 (t, 2H, J=7.7 Hz), 7.38-7.34 (t, 2H, J=7.7 Hz), 7.24-7.21 (d, 1H, J=7.4 Hz), 7.15 (m, 1H), 6.94-6.90 (dd, 1H, J=3, 7 Hz), 4.28-4.24 (t, 2H, J=6 Hz), 2.47-2.43 (t, 2H, J=6 Hz). MS (DCI/NH3) 275 (M+NH4)+. Anal. Calcd for C15H15NO3 ·0.25H2O: C, 68.82; H, 55.96; N, 5.35. Found: C, 68.92; H, 5.87; N, 5.33.

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 aqueous hydroxylamine (3.34 mmol
  6. customprepared
  7. customThe reaction mixture was quenched with 1:1 dichloromethane-saturated aqueous NH4Cl
  8. washThe aqueous phase was washed with brine
  9. dry with materialdried over Na2SO4
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo
  12. waitleft
  13. waitstanding at -30° C. for 3 days
  14. customThe resulting crystals were collected

Sources & evidence

ORD record
ord-8f202a2be3684014a4e085c620e0910f
Source dataset
uspto-grants-1997_09
Patent number
US05665777

Reaction notes

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