N-(2-(hydroxymethyl)phenyl)methanesulfonamide → 2-(Methylsulfonamido)benzaldehyde
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
Product 1
Reagents, catalysts & solvents 2
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
- filtrationfiltered through a pad of Celite
- washThe pad was washed with dichloromethane/methanol (1:1)
- 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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