(2-Chloro-3-nitrophenyl)methanol → 2-Chloro-3-nitrobenzaldehyde

HRID 877215Notes

Reaction equation

HRID 877215 reaction equation
[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.[Cl:12][C:13]1[C:18]([N+:19]([O-:21])=[O:20])=[CH:17][CH:16]=[CH:15][C:14]=1[CH2:22][OH:23]>ClCCl>[Cl:12][C:13]1[C:18]([N+:19]([O-:21])=[O:20])=[CH:17][CH:16]=[CH:15][C:14]=1[CH:22]=[O:23]

Participants

4

Reactant 2

HCID 15132843(2-Chloro-3-nitrophenyl)methanolHCID 178418287HCID 178418287, compound

Product 1

HCID 126677132-Chloro-3-nitrobenzaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

8.43 g (39.09 mmol) of pyridinium chlorochromate (PCC) were added to a solution of 6.11 g (32.57 mmol) of (2-chloro-3-nitrophenyl)methanol in 120 ml of dichloromethane, and the mixture was stirred at room temperature for 12 hours. After complete conversion, the solvent was evaporated to dryness under reduced pressure. The residue obtained was purified chromatographically on silica gel (mobile phase dichloromethane/methanol 20:1). This gave 4.82 g (25.97 mmol, 79.7% of theory) of the title compound.

Workup

  1. customAfter complete conversion, the solvent was evaporated to dryness under reduced pressure
  2. customThe residue obtained
  3. customwas purified chromatographically on silica gel (mobile phase dichloromethane/methanol 20:1)

Sources & evidence

ORD record
ord-660e4a98140b4d29a13b8028de20f679
Source dataset
uspto-grants-2015_03
Patent number
US08987256B2

Reaction notes

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