4-(Bromomethyl)benzyl alcohol → 4-(Bromomethyl)benzaldehyde

HRID 1289172Notes

Reaction equation

HRID 1289172 reaction equation
[Br:1][CH2:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][OH:8])=[CH:5][CH:4]=1.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>ClCCl>[Br:1][CH2:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=[O:8])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 103304344-(Bromomethyl)benzyl alcoholHCID 178418287HCID 178418287, compound

Product 1

HCID 112064214-(Bromomethyl)benzaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

The 4-bromomethylbenzyl alcohol (57.91 g, 288.0 mmol) was then converted to the corresponding aldehyde by dissolving the intermediate in 350 ml of dichloromethane and then adding this solution to a flask containing pyridinium chlorochromate (93.0 g, 431 mmol) suspended in 750 ml of dichloromethane. The dark-brown reaction mixture was then stirred at room temperature under nitrogen atmosphere. After 70 minutes of stirring most of the starting material had been consumed as determined by thin layer chromatography.

Workup

  1. additionadding this solution to a flask
  2. stirringAfter 70 minutes of stirring most of the starting material
  3. customhad been consumed

Sources & evidence

ORD record
ord-e69c653380c14a5e8864ce2a9fa8c3f1
Source dataset
uspto-grants-1998_05
Patent number
US05747517

Reaction notes

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