Sulfuric Acid → HCID 21438365, compound
Reaction equation
[F:1][C:2]([F:23])([F:22])[S:3]([C:6]1[CH:11]=[CH:10][C:9]([S:12][C:13]2[CH:21]=[CH:20][CH:19]=[CH:18][C:14]=2[C:15]([OH:17])=O)=[CH:8][CH:7]=1)(=[O:5])=[O:4].S(=O)(=O)(O)O>>[F:23][C:2]([F:1])([F:22])[S:3]([C:6]1[CH:7]=[CH:8][C:9]2[S:12][C:13]3[C:14](=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:15](=[O:17])[C:10]=2[CH:11]=1)(=[O:5])=[O:4]Participants
Procedure
A solution of 7.6 g. (0.021 mol) of 2-(4-trifluoromethylsulfonylphenylthio)benzoic acid in 40 ml. of concentrated sulfuric acid is stirred and heated on a steam bath for 1.5 hours. After cooling to room temperature, the solution is slowly poured onto 400 g. of crushed ice. The oil that precipitates is extracted with three 150 ml. portions of an ether-benzene mixture. The combined organic extracts are washed four times with water and three times with dilute sodium bicarbonate solution. The ether-benzene layer is dried over magnesium sulfate, filtered, and evaporated to dryness on a rotary evaporator. The pale yellow solid obtained is recrystallized from acetonitrile to give 2-(trifluoromethylsulfonyl)thioxanthen-9-one, m.p. 163°-164.5°.
Workup
- temperatureheated on a steam bath for 1.5 hours
- additionthe solution is slowly poured onto 400 g
- customThe oil that precipitates
- extractionis extracted with three 150 ml
- washThe combined organic extracts are washed four times with water and three times with dilute sodium bicarbonate solution
- dry with materialThe ether-benzene layer is dried over magnesium sulfate
- filtrationfiltered
- customevaporated to dryness on a rotary evaporator
- customThe pale yellow solid obtained
- customis recrystallized from acetonitrile
Sources & evidence
- ORD record
- ord-0ab7085513084761b7efb1e384465d71
- Source dataset
- uspto-grants-1977_05
- Patent number
- US04021561
Reaction notes
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