3-Iodobenzyl alcohol → 3-Iodobenzaldehyde

HRID 420416Notes

Reaction equation

HRID 420416 reaction equation
[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.[I:12][C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=1)[CH2:16][OH:17]>ClCCl.CCOCC>[I:12][C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=1)[CH:16]=[O:17]

Participants

5

Reactant 2

HCID 423003-Iodobenzyl alcoholHCID 178418287HCID 178418287, compound

Product 1

HCID 2526103-IodobenzaldehydeYield 95%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

A suspension of pyridinium chlorochromate (2.45 g, 11.4 mmol) and dry celite (˜2.00 g) in dry dichloromethane (20 ml) was stirred at room temperature for 15 min. 3-Iodobenzyl alcohol (11) (1.02 g, 4.35 mmol) in dry dichloromethane (5 ml) was added. The suspension was shielded from light and stirred at room temperature for 2 h after which it was diluted with ether, and filtered through celite. The cloudy brown filtrate was concentrated to a red-brown gummy paste which was re-dissolved in dichloromethane and passed through a short silica column, eluting with dichloromethane. This gave a clear, colourless solution which was concentrated to give 3-iodobenzaldehyde (12) as a white solid (0.953 g, 95%).

Workup

  1. dry with materialdry celite (˜2.00 g) in dry dichloromethane (20 ml)
  2. stirringstirred at room temperature for 2 h after which it
  3. filtrationfiltered through celite
  4. concentrationThe cloudy brown filtrate was concentrated to a red-brown gummy paste which
  5. dissolutionwas re-dissolved in dichloromethane
  6. washeluting with dichloromethane
  7. customThis gave a clear, colourless solution which
  8. concentrationwas concentrated

Sources & evidence

ORD record
ord-d123252ca6e341bd851cfa9b7331d59b
Source dataset
uspto-grants-2012_01
Patent number
US08097238B2

Reaction notes

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