Réaction #1161

ord-6d44d87ee23a4984ad13cff1877a23a4

Équation de réaction

CC(=O)O
acetic acid
[K+].[O]=[Mn](=[O])(=[O])[O-]
KMnO4
CSc1ccc(C(C)=O)cc1
4-(methylthio)acetophenone
O=S([O-])[O-].[Na+].[Na+]
sodium sulfite
→
CC(=O)c1ccc(S(C)(=O)=O)cc1
4-(methylsulfonyl)acetophenone

Réactifs

CC(=O)O
acetic acid
[K+].[O]=[Mn](=[O])(=[O])[O-]
KMnO4
CSc1ccc(C(C)=O)cc1
4-(methylthio)acetophenone
O=S([O-])[O-].[Na+].[Na+]
sodium sulfite

Réactifs

Aucun

Solvants

O
water
O
water

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    Autreto return to room temperature
  2. 2
    workup.WAITThis is left
  3. 3
    AutreThe solid obtained
  4. 4
    Filtrationis filtered off
  5. 5
    Lavagewashed copiously with water
  6. 6
    Autrerecrystallized from 95% ethanol

Mode opératoire

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.

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US05723485uspto-grants-1998_03