Acetic Acid → p-(Methylsulphonyl)benzoic acid
Reaction equation
CS[C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=1.[C:12](O)(=O)C.OO.[S:18]([O-:21])([O-])=[O:19].[Na+].[Na+]>O>[CH3:12][S:18]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=1)(=[O:21])=[O:19]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of 5 g of 4-(methylthio)benzoic acid (97%) and 30 mL of glacial acetic acid was formed. The mixture was cooled in a water bath containing a small amount of ice. To the mixture was added 8.5 g of 30% hydrogen peroxide gradually over one hour. No temperature rise was observed during the addition of the hydrogen peroxide. The reaction mixture was then heated for one and a half hours with the temperature ranging between 70° C. and 100° C. Heating was stopped and the reaction mixture was allowed to cool to room temperature. A solid was present in the reaction mixture. A solution of 3 g of sodium sulfite in 57 g of water was added to the reaction mixture. The solid was filtered from solution and was washed three times with cold deionized water. The solid was transferred to a watchglass and dried overnight. The dried product weighed 5.25 g which is a yield of 88.1% of the theoretical based upon the amount of the starting benzoic acid.
Workup
- temperatureThe mixture was cooled in a water bath
- additioncontaining a small amount of ice
- temperatureThe reaction mixture was then heated for one and a half hours with the temperature
- customranging between 70° C. and 100° C
- temperatureHeating
- filtrationThe solid was filtered from solution
- washwas washed three times
- customdried overnight
Sources & evidence
- ORD record
- ord-2cedec505ebe4ddc8fe9707a5a94bedc
- Source dataset
- uspto-grants-1994_11
- Patent number
- US05364959
Reaction notes
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