Methyl 3-(hydroxymethyl)-5-iodobenzoate → Methyl 3-formyl-5-iodobenzoate

HRID 1740306Notes

Reaction equation

HRID 1740306 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]([I:13])[CH:6]=[C:7]([CH:12]=1)[C:8]([O:10][CH3:11])=[O:9]>C(OCC)(=O)C.[O-2].[O-2].[Mn+4]>[CH:2]([C:3]1[CH:4]=[C:5]([I:13])[CH:6]=[C:7]([CH:12]=1)[C:8]([O:10][CH3:11])=[O:9])=[O:1]

Participants

4

Reactant 1

HCID 21837989Methyl 3-(hydroxymethyl)-5-iodobenzoate

Product 1

HCID 21838328Methyl 3-formyl-5-iodobenzoateYield 55.8%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

The mixture of methyl 5-hydroxymethyl-3-iodobenzoate (5.0 g) and manganese dioxide (30.0 g) in ethyl acetate (50.0 ml) was heated under reflux for 4 hours. The magnganese dioxide was removed by filtration and the filtrate was evaporated in vacuo to give methyl 5-formyl-3-iodobenzoate (2.77 g).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 4 hours
  3. customThe magnganese dioxide was removed by filtration
  4. customthe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-8198add690444a2cb28721a0145655f5
Source dataset
uspto-grants-1999_10
Patent number
US05968985

Reaction notes

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