N-(2-(hydroxymethyl)phenyl)methanesulfonamide → 2-(Methylsulfonamido)benzaldehyde

HRID 58858Notes

Reaction equation

HRID 58858 reaction equation
[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH:9][S:10]([CH3:13])(=[O:12])=[O:11]>ClCCl.[O-2].[O-2].[Mn+4]>[CH:2]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH:9][S:10]([CH3:13])(=[O:12])=[O:11])=[O:1]

Participants

4

Reactant 1

HCID 22955815N-(2-(hydroxymethyl)phenyl)methanesulfonamide

Product 1

HCID 115793042-(Methylsulfonamido)benzaldehydeYield 78%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

Manganese dioxide (85%, 45.0 g, 0.52 mol) was added to a solution of N-[2-(hydroxymethyl)phenyl]methanesulfonamide (13.0 g, 65 mmol) in dichloromethane (200 mL) at ambient temperature under nitrogen. The reaction mixture was stirred for 12 h and then filtered through a pad of Celite. The pad was washed with dichloromethane/methanol (1:1) and the combined organics were concentrated to afford N-(2-Formylphenyl)methanesulfonamide (10.1 g, 78% yield) as a yellow solid.

Workup

  1. filtrationfiltered through a pad of Celite
  2. washThe pad was washed with dichloromethane/methanol (1:1)
  3. concentrationthe combined organics were concentrated

Sources & evidence

ORD record
ord-ae6c17ba7cc94172bce5cf4448f0718c
Source dataset
uspto-grants-2016_09
Patent number
US09434761B2

Reaction notes

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