Acetic Acid → 4-(Methylsulfonyl)benzonitrile

HRID 584125Notes

Reaction equation

HRID 584125 reaction equation
CS[C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][CH:4]=1.[Mn]([O-])(=O)(=O)=O.[K+].[OH:17][S:18]([O-:20])=O.[Na+].[CH3:22]C(O)=O>>[CH3:22][S:18]([C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][CH:4]=1)(=[O:20])=[O:17]

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 516875Potassium PermanganateHCID 5909604-(Methylthio)benzonitrileHCID 23665763Sodium Bisulfite

Product 1

HCID 5199814-(Methylsulfonyl)benzonitrileYield 82%

Procedure

4-Methylsulfanyl-benzonitrile (250 mg, 1.68 mmol) was dissolved in 12 mL of HOAc. Potassium permanganate (531 mg, 3.36 mmol) was added as an aqueous solution (7-8 mL). After stirring 30 min at RT, NaHSO3 was added with stirring until the brown color of the solution disappeared. The mixture was concentrated and diluted with water. The precipitate was filtered and dried in vacuo to yield 4-methanesulfonyl-benzonitrile (250 mg, 82%) which was used without further purification.

Workup

  1. stirringwith stirring until the brown color of the solution
  2. concentrationThe mixture was concentrated
  3. additiondiluted with water
  4. filtrationThe precipitate was filtered
  5. customdried in vacuo

Sources & evidence

ORD record
ord-9846733ca9f24b588cde6fd012db9f92
Source dataset
uspto-grants-2005_08
Patent number
US06924284B2

Reaction notes

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