4-Toluenesulfonyl chloride → HCID 19700284, compound

HRID 861832Notes

Reaction equation

HRID 861832 reaction equation
[H-].[Na+].[F:3][C:4]([F:15])([F:14])[C:5]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([OH:7])[CH3:6].[C:16]1([CH3:26])[CH:21]=[CH:20][C:19]([S:22](Cl)(=[O:24])=[O:23])=[CH:18][CH:17]=1>C(OCC)C>[F:3][C:4]([F:14])([F:15])[C:5]([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)([O:7][S:22]([C:19]1[CH:20]=[CH:21][C:16]([CH3:26])=[CH:17][CH:18]=1)(=[O:24])=[O:23])[CH3:6]

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 24758Sodium hydrideHCID 1235801,1,1-trifluoro-2-phenylpropan-2-ol

Product 1

HCID 19700284HCID 19700284, compoundYield 49.9%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

0.9 g (30 mmol) of sodium hydride (80% strength dispersion in mineral oil) was added to 5 g (26 mmol) of 1,1,1-trifluoro-2-phenylpropan-2-ol in 125 ml of diethyl ether at room temperature. The mixture was stirred for about 1 hour, and 4.75 g (25 mmol) of toluene-4-sulfonyl chloride were then added in portions. Stirring was carried out for 60 hours at room temperature, after which the undissolved constituents were filtered off and the solution was then cooled. 4.3 g of 1,1,1-trifluoro-2-phenyl-2-(toluene-4-sulfonyloxy)-propane were obtained (colorless crystals, m.p.: 102° C. [recrystallized from diethyl ether]). After the mother liquor had been evaporated down, a further 1.6 g of the desired compound could be isolated.

Workup

  1. stirringStirring
  2. waitwas carried out for 60 hours at room temperature
  3. filtrationafter which the undissolved constituents were filtered off
  4. temperaturethe solution was then cooled

Sources & evidence

ORD record
ord-10cff1f474ae4931bea99c2f0a138022
Source dataset
uspto-grants-1998_02
Patent number
US05716756

Reaction notes

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