(4-Iodo-3-propoxyphenyl)methanol → 4-Iodo-3-propoxybenzaldehyde

HRID 390647Notes

Reaction equation

HRID 390647 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][OH:9])=[CH:4][C:3]=1[O:10][CH2:11][CH2:12][CH3:13]>ClCCl.[O-2].[Mn+2]>[I:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[O:9])=[CH:4][C:3]=1[O:10][CH2:11][CH2:12][CH3:13]

Participants

4

Reactant 1

HCID 68960017(4-Iodo-3-propoxyphenyl)methanol

Product 1

HCID 866260984-Iodo-3-propoxybenzaldehydeYield 57%

Reagents, catalysts & solvents 2

HCID 160959Manganese oxideCatalystHCID 6344DichloromethaneSolvent

Procedure

The (4-iodo-3-propoxyphenyl)methanol is dissolved in 30 mL of dichloromethane and 3.9 g (45 mmol) of manganese oxide are added. The reaction medium is stirred for 12 hours at room temperature. After filtering off the solid through Celite, the filtrate is evaporated under vacuum. The residue obtained is purified by chromatography on a column of silica eluted with a 9/1 heptane/ethyl acetate mixture. 1.5 g (57% yield for the three steps a-c) of 4-iodo-3-propoxybenzaldehyde are obtained.

Workup

  1. filtrationAfter filtering off the solid through Celite
  2. customthe filtrate is evaporated under vacuum
  3. customThe residue obtained
  4. customis purified by chromatography on a column of silica
  5. washeluted with a 9/1 heptane/ethyl acetate mixture

Sources & evidence

ORD record
ord-def1e0975f704613bcce512a50350be1
Source dataset
uspto-grants-2013_02
Patent number
US08383652B2

Reaction notes

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