(3-Butoxy-4-iodophenyl)methanol → 3-Butoxy-4-iodobenzaldehyde

HRID 390626Notes

Reaction equation

HRID 390626 reaction equation
[CH2:1]([O:5][C:6]1[CH:7]=[C:8]([CH2:13][OH:14])[CH:9]=[CH:10][C:11]=1[I:12])[CH2:2][CH2:3][CH3:4]>ClCCl.[O-2].[O-2].[Mn+4]>[CH2:1]([O:5][C:6]1[CH:7]=[C:8]([CH:9]=[CH:10][C:11]=1[I:12])[CH:13]=[O:14])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 1

HCID 59574926(3-Butoxy-4-iodophenyl)methanol

Product 1

HCID 595749303-Butoxy-4-iodobenzaldehydeYield 73.4%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

21.2 g (207 mmol) of manganese dioxide are added to 10.6 g (34.5 mmol) of (3-butoxy-4-iodophenyl)methanol in 70 mL of dichloromethane. The reaction mixture is stirred at room temperature for 2 days. The reaction medium is filtered through Celite. The filtrate is evaporated and the oil obtained (9.45 g) is purified by chromatography on silica gel eluted with a 90/10 heptane/ethyl acetate mixture. 7.7 g (73%) of 3-butoxy-4-iodobenzaldehyde are obtained in the form of a yellow oil.

Workup

  1. filtrationThe reaction medium is filtered through Celite
  2. customThe filtrate is evaporated
  3. customthe oil obtained (9.45 g)
  4. customis purified by chromatography on silica gel
  5. washeluted with a 90/10 heptane/ethyl acetate mixture

Sources & evidence

ORD record
ord-553b0dd1c9ca482cadb3f5dec4c37543
Source dataset
uspto-grants-2013_02
Patent number
US08383652B2

Reaction notes

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