Hydroxyamine hydrochloride → 1-[2,4-Bis(benzyloxy)-6-(4-nitrophenoxy)phenyl]-N-hydroxyethanimine

HRID 880367Notes

Reaction equation

HRID 880367 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:12]=[C:11]([O:23][C:24]2[CH:29]=[CH:28][C:27]([N+:30]([O-:32])=[O:31])=[CH:26][CH:25]=2)[C:10]=1C(=O)C)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:36][OH:37].Cl.[CH3:39][C:40](O[Na])=O>C(O)C.C(O)(=O)C>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([O:15][CH2:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:12]=[C:11]([O:23][C:24]2[CH:25]=[CH:26][C:27]([N+:30]([O-:32])=[O:31])=[CH:28][CH:29]=2)[C:10]=1[C:40](=[N:36][OH:37])[CH3:39])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 667590791-[2,4-Bis(benzyloxy)-6-(4-nitrophenoxy)phenyl]ethanoneHCID 178418247HCID 178418247, compound

Product 1

HCID 866623761-[2,4-Bis(benzyloxy)-6-(4-nitrophenoxy)phenyl]-N-hydroxyethanimineYield 88%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

A stirred solution of 1-[2,4-bis(benzyloxy)-6-(4-nitrophenoxy)phenyl]ethanone (15 g, 32 mmol), NH2OH.HCl (3 g, 42 mmol) and CH3COONa (3.5 g, 42 mmol) in ethanol (150 mL) and acetic acid (250 mL) was refluxed for 5 hours. The solvent was removed and the residue taken up in ethyl acetate was thoroughly washed with 2 M NaHCO3 solution then with brine. After drying over Na2SO4, the solvent was removed and the oily residue was filtered on a small pad of silica gel eluting with hexane/ethyl acetate 6/3 to provide the title compound (13.3 g, 88% yield).

Workup

  1. customThe solvent was removed
  2. washwas thoroughly washed with 2 M NaHCO3 solution
  3. dry with materialAfter drying over Na2SO4
  4. customthe solvent was removed
  5. filtrationthe oily residue was filtered on a small pad of silica gel eluting with hexane/ethyl acetate 6/3

Sources & evidence

ORD record
ord-44092914dbbf42dcb2f68e215cb47666
Source dataset
uspto-grants-2015_03
Patent number
US08993556B2

Reaction notes

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