Acetic Acid → 4-Methylsulfonylacetophenone

HRID 1065

Reaction equation

HRID 1065 reaction equation
[O-][Mn](=O)(=O)=O.[K+].[CH3:7][C:8]([C:10]1[CH:15]=[CH:14][C:13](SC)=[CH:12][CH:11]=1)=[O:9].[S:18]([O-:21])([O-])=[O:19].[Na+].[Na+].[C:24](O)(=O)C>O>[CH3:7][C:8]([C:10]1[CH:15]=[CH:14][C:13]([S:18]([CH3:24])(=[O:21])=[O:19])=[CH:12][CH:11]=1)=[O:9]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 24437Sodium SulfiteHCID 745011-(4-(Methylthio)phenyl)ethan-1-oneHCID 516875Potassium Permanganate

Product 1

HCID 825294-Methylsulfonylacetophenone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A solution of 152 g (0.96 mol) of KMnO4 in 3.5 1 of water is introduced into a mixture of 117.1 g (0.7 mol) of 4-(methylthio)acetophenone, prepared in Example 2c, and 292 ml of acetic acid. 2.3 l of water are added and the reaction temperature is allowed to return to room temperature. Saturated sodium sulfite solution is added dropwise until the solution is decolorized. This is left to stand overnight at room temperature. The solid obtained is filtered off, washed copiously with water and recrystallized from 95% ethanol to give 91.5 g of 4-(methylsulfonyl)acetophenone.

Workup

  1. customto return to room temperature
  2. waitThis is left
  3. customThe solid obtained
  4. filtrationis filtered off
  5. washwashed copiously with water
  6. customrecrystallized from 95% ethanol

Sources & evidence

ORD record
ord-6d44d87ee23a4984ad13cff1877a23a4
Source dataset
uspto-grants-1998_03
Patent number
US05723485

Linked notes

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