2-(Hydroxymethyl)-4-iodophenol → 5-Iodosalicylaldehyde

HRID 650147Notes

Reaction equation

HRID 650147 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:7]([I:10])=[CH:6][C:3]=1[CH2:4][OH:5]>CC(C)=O.[O-2].[Mn+4].[O-2]>[OH:1][C:2]1[CH:9]=[CH:8][C:7]([I:10])=[CH:6][C:3]=1[CH:4]=[O:5]

Participants

4

Reactant 1

HCID 125452592-(Hydroxymethyl)-4-iodophenol

Product 1

HCID 2526125-IodosalicylaldehydeYield 58%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 180AcetoneSolvent

Procedure

To a stirred solution of 2-hydroxy-5-iodobenzyl alcohol (43.5 g, 174.0 mmol) in acetone (700 mL) was added 85% activated manganese(IV) oxide (5 micron, 50 g, 494.0 mmol) and the solution stirred at room temperature for 16 hours. The manganese oxide was removed by filtration through diatomaceous earth and the filtrate concentrated in vacuo. The product was purified by flash silica chromatography (0-20% ethyl acetate in hexanes) The 2-hydroxy-5-iodobenzaldehyde was obtained as a greenish-yellow solid (24.3 g, 58%). A small amount of the 2-hydroxy-5-iodobenzaldehyde was recrystallized from methanol/water to afford an analytical sample and the remainder of the compound was used without further purification: mp 99-101° C. 1H NMR (CDCl3/300 MHz) 9.83 (s, 1H), 7.79 (d, 1H, J=2.2 Hz), 7.77 (dd, 1H, J=8.7 Hz, J=2.2 Hz), 6.81 (d, 1H, J=8.7 Hz). ESHRMS 246.9229 (M−H Calc'd 246.9256).

Workup

  1. customThe manganese oxide was removed by filtration through diatomaceous earth
  2. concentrationthe filtrate concentrated in vacuo
  3. customThe product was purified by flash silica chromatography (0-20% ethyl acetate in hexanes) The 2-hydroxy-5-iodobenzaldehyde

Sources & evidence

ORD record
ord-d75218f50aa0470e9e4004ba7f96150e
Source dataset
uspto-grants-2001_08
Patent number
US06271253B1

Reaction notes

Loading…