2,2,3,3,3-Pentafluoropropanol → 2,2,3,3,3-Pentafluoropropyl p-Toluenesulfonate

HRID 1975806Notes

Reaction equation

HRID 1975806 reaction equation
[F:1][C:2]([F:9])([C:5]([F:8])([F:7])[F:6])[CH2:3][OH:4].[Cl-].[C:11]1([CH3:21])[CH:16]=[CH:15][C:14]([S:17]([O-])(=[O:19])=[O:18])=[CH:13][CH:12]=1.[OH-].[Na+]>O>[F:1][C:2]([F:9])([C:5]([F:8])([F:7])[F:6])[CH2:3][O:4][S:17]([C:14]1[CH:15]=[CH:16][C:11]([CH3:21])=[CH:12][CH:13]=1)(=[O:19])=[O:18]

Participants

5

Reactant 3

HCID 98722,2,3,3,3-PentafluoropropanolHCID 14798Sodium HydroxideHCID 22024621p-Toluenesulfonate chloride

Product 1

HCID 27760172,2,3,3,3-Pentafluoropropyl p-ToluenesulfonateYield 82.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
50 °C

Procedure

2,2,3,3,3-pentafluoro-1-propanol (300.8 g) was added to p-toluenesulfonate chloride(400.66 g, 2.10 mol) in water at 25° C. The mixture was heated in a 5 liter, 3-neck separatory funnel type reaction flask, under mechanical stirring, to a temperature of 50° C. Sodium hydroxide(92.56 g, 2.31 mol) in 383 ml water (6M solution) was added dropwise to the reaction mixture via addition funnel over a period of 2.5 hours, keeping the temperature below 55° C. Upon completion of this addition, when the pH of the aqueous phase was approximately 6, the organic phase was drained from the flask while still warm, and allowed to cool to 25° C. The crude product was recrystallized from petroleum ether to afford white needles of 2,2,3,3,3-pentafluoropropyl-p-toluenesulfonate (500.7 g, 1.65 mol, 82.3%).

Workup

  1. customthe temperature below 55° C
  2. additionUpon completion of this addition, when the pH of the aqueous phase
  3. temperaturewhile still warm
  4. temperatureto cool to 25° C
  5. customThe crude product was recrystallized from petroleum ether

Sources & evidence

ORD record
ord-30cfa33ae8234d9e98d6e1e1a6529f4c
Source dataset
uspto-grants-1994_02
Patent number
US05288819

Reaction notes

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