Iodine → 2-Hydroxy-3-iodo-4-methoxybenzaldehyde

HRID 855022Notes

Reaction equation

HRID 855022 reaction equation
[OH:1][C:2]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].II.[I:14](O)(=O)(=O)=O.C(OCC)(=O)C>C(O)C.O>[OH:1][C:2]1[C:9]([I:14])=[C:8]([O:10][CH3:11])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5]

Participants

7

Reactant 4

HCID 807IodineHCID 8857Ethyl AcetateHCID 65185Metaperiodic acidHCID 696002-Hydroxy-4-Methoxybenzaldehyde

Product 1

HCID 190890572-Hydroxy-3-iodo-4-methoxybenzaldehydeYield 49%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
68 °C

Procedure

To a solution of 4.0 g (26.3 mmol) of 2-hydroxyl-4-methoxybenzaldehyde in 30 mL of ethanol was added 1.87 g (7.4 mmol) of iodine, followed by addition of a solution of 6 g (26.3 mmol) of periodic acid in 10 mL of water. The resulting dark yellow solution was heated to 68° C. for two h. After cooling to room temperature, the reaction was added to 300 mL of ethyl acetate. The resulting organic solution was washed with saturated aqueous solution of sodium sulfite, washed with brine and dried over anhydrous magnesium sulfate. After removing the volatiles, the crude products were purified by silica chromatography to afford 1.8 g (49%) of a light yellow solid: 1H NMR(CDCl3/400 MHz,) 12.18(s, 1H), 9.63(s, 1H), 7.53(d, J=8.4 Hz, 1H), 6.56(d, J=8.4 Hz, 1H), 3.99(s, 3H). 13C NMR (CDCl3/400 MHz) 194.2, 165.3, 163.0, 136.3, 116.1, 103.6, 57.2. MS (ESI+) 278.9(M+1, 100).

Workup

  1. temperatureAfter cooling to room temperature
  2. washThe resulting organic solution was washed with saturated aqueous solution of sodium sulfite
  3. washwashed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customAfter removing the volatiles
  6. customthe crude products were purified by silica chromatography

Sources & evidence

ORD record
ord-bd8a5cc0bcc44aada70c09ced8b4b17c
Source dataset
uspto-grants-2007_08
Patent number
US07259266B2

Reaction notes

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