(3-Amino-5-ethoxy-4-iodo-phenyl)-methanol → 3-Amino-5-ethoxy-4-iodo-benzaldehyde

HRID 502369Notes

Reaction equation

HRID 502369 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH2:12][OH:13])[CH:5]=[C:6]([O:9][CH2:10][CH3:11])[C:7]=1[I:8]>ClCCl.O=[Mn]=O>[NH2:1][C:2]1[C:7]([I:8])=[C:6]([O:9][CH2:10][CH3:11])[CH:5]=[C:4]([CH:3]=1)[CH:12]=[O:13]

Participants

4

Reactant 1

HCID 68454929(3-Amino-5-ethoxy-4-iodo-phenyl)-methanol

Product 1

HCID 587063533-Amino-5-ethoxy-4-iodo-benzaldehydeYield 64.5%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of (3-amino-5-ethoxy-4-iodo-phenyl)-methanol (4.9 g, 16.72 mmol) in dichloromethane (100 mL) was added MnO2 (7.27 g, 83.59 mmol) and the reaction mixture heated to reflux for 3 h. Filtration through Hyflo, concentration by evaporation under reduced pressure and purification with column chromatography on silica eluting with hexane/ethyl acetate (3:1) yielded 3.14 g (60%) of the title compound.

Workup

  1. temperaturethe reaction mixture heated
  2. temperatureto reflux for 3 h
  3. filtrationFiltration
  4. concentrationthrough Hyflo, concentration
  5. customby evaporation
  6. customunder reduced pressure and purification with column chromatography on silica eluting with hexane/ethyl acetate (3:1)

Sources & evidence

ORD record
ord-4b381e181b04483f8ff3dce4079b2db3
Source dataset
uspto-grants-2010_08
Patent number
US07772253B2

Reaction notes

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