4-Chlorobenzaldehyde → 4-(Methylsulfonyl)benzaldehyde

HRID 908164Notes

Reaction equation

HRID 908164 reaction equation
Cl[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[Na+].[CH3:11][S:12]([O-:14])=[O:13]>CS(C)=O>[CH3:11][S:12]([C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1)(=[O:14])=[O:13]

Participants

4

Reactant 2

HCID 77264-ChlorobenzaldehydeHCID 2733271Sodium methanesulfinate

Product 1

HCID 2203764-(Methylsulfonyl)benzaldehydeYield 33.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
100 °C

Procedure

4-Chlorobenzaldehyde (5.0 g, 36 mmol) and methanesulfinic acid sodium salt (4.04 g, 40 mmol) are dissolved in dry DMSO under argon. The stirred reaction mixture is heated at 100° C. for 17 hours then poured onto water (50 ml). The white precipitate is removed by filtration and dried under vacuum to afford the title compound (2.2 g).

Workup

  1. customThe stirred reaction mixture
  2. additionthen poured onto water (50 ml)
  3. customThe white precipitate is removed by filtration
  4. customdried under vacuum

Sources & evidence

ORD record
ord-f46b7d7f7cf94f7fa94a6296c1a5a44f
Source dataset
uspto-grants-2011_09
Patent number
US08017608B2

Reaction notes

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