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

HRID 250843Notes

Reaction equation

HRID 250843 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH2:16][OH:17])[CH:12]=[CH:13][C:14]=1[I:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>ClCCl.[O-2].[Mn+2]>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:12]=[CH:13][C:14]=1[I:15])[CH:16]=[O:17])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 45140291(3-Benzyloxy-4-iodophenyl)methanol

Product 1

HCID 534172453-(Benzyloxy)-4-iodobenzaldehydeYield 54%

Reagents, catalysts & solvents 2

HCID 160959Manganese oxideCatalystHCID 6344DichloromethaneSolvent

Procedure

7.8 g (90 mmol, 5 eq) of manganese oxide are added to a solution of 6.5 g (17.98 mmol, 1 eq) of (3-benzyloxy-4-iodophenyl)methanol in 50 mL of dichloromethane. The reaction medium is stirred for 12 hours at room temperature, and the solid is then filtered off and the solvent is evaporated off. The residual oil is chromatographed on silica gel (8/2 heptane/ethyl acetate). The oil obtained is crystallized from pentane. 3.25 g of 3-benzyloxy-4-iodobenzaldehyde are obtained. Yield=54% for the three steps c, d and e.

Workup

  1. filtrationthe solid is then filtered off
  2. customthe solvent is evaporated off
  3. customThe residual oil is chromatographed on silica gel (8/2 heptane/ethyl acetate)
  4. customThe oil obtained
  5. customis crystallized from pentane

Sources & evidence

ORD record
ord-13eb22f67d1b4435aa2fe080be85e975
Source dataset
uspto-grants-2011_01
Patent number
US07863332B2

Reaction notes

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