2,2,3,3-Tetrafluoro-1-propanol → 2,2,3,3-Tetrafluoropropyl 4-toluenesulfonate
Reaction equation
[F:1][C:2]([F:8])([CH:5]([F:7])[F:6])[CH2:3][OH:4].[S:9](Cl)([C:12]1[CH:18]=[CH:17][C:15]([CH3:16])=[CH:14][CH:13]=1)(=[O:11])=[O:10].[OH-].[Na+]>O>[F:1][C:2]([F:8])([CH:5]([F:7])[F:6])[CH2:3][O:4][S:9]([C:12]1[CH:18]=[CH:17][C:15]([CH3:16])=[CH:14][CH:13]=1)(=[O:11])=[O:10]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
2,2,3,3-tetrafluoropropanol(406 g, 3.08 mol), 613 g tosyl chloride(3.22 mol), and 1200 ml water heated to 50° C. with mechanical stirring. Sodium hydroxide(139.7 g, 3.5 ml) in 560 ml water was added at a rate such that the temperature remained less than 65° C. After the addition was completed, the mixture was stirred at 50° C. until the pH of the aqueous phase was 6. The mixture was cooled and extracted with 1.5 liters methylene chloride. The organic layer was washed twice with 200 ml aqueous ammonia, 350 ml water, dried with magnesium sulfate, and distilled to give 697.2 g(79%) viscous oil.
Workup
- customremained less than 65° C
- additionAfter the addition
- temperatureThe mixture was cooled
- extractionextracted with 1.5 liters methylene chloride
- washThe organic layer was washed twice with 200 ml aqueous ammonia, 350 ml water
- dry with materialdried with magnesium sulfate
- distillationdistilled
Sources & evidence
- ORD record
- ord-9f6914a8ac5c417195915ed44aaf4284
- Source dataset
- uspto-grants-1994_02
- Patent number
- US05288819
Reaction notes
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