Hydrochloric Acid → 3,3,3-Trifluoro-1-(p-toluene-sulfonyloxy)-2-trifluoromethylpropan-2-ol

HRID 2360750Notes

Reaction equation

HRID 2360750 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([OH:11])(=[O:10])=[O:9])=[CH:6][CH:7]=1.[F:12][C:13]([F:23])([F:22])[C:14]([C:18]([F:21])([F:20])[F:19])([OH:17])[CH2:15]O.Cl.C1(C)C=CC=CC=1>N1C=CC=CC=1>[F:12][C:13]([F:22])([F:23])[C:14]([C:18]([F:19])([F:21])[F:20])([OH:17])[CH2:15][O:9][S:8]([C:5]1[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][CH:6]=1)(=[O:11])=[O:10]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1140TolueneHCID 6101p-Toluenesulfonic acidHCID 118056773,3,3-Trifluoro-2-(trifluoromethyl)-1,2-propanediol

Product 1

HCID 717225883,3,3-Trifluoro-1-(p-toluene-sulfonyloxy)-2-trifluoromethylpropan-2-olYield 74%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

Under ice cooling, a solution of 54 g of p-toluene sulfonate in 140 g of pyridine was added dropwise to a mixture of 93 g of the 61 wt % IPE solution of 3,3,3-trifluoro-2-trifluoromethyl-1,2-propane diol prepared in Reference Synthesis Example and 140 g of pyridine. Stirring was continued for 48 hours at room temperature. The reaction solution was ice cooled and poured into a mixture of 678 g of 20 wt % hydrochloric acid aqueous solution and 100 g of ice to quench the reaction. Toluene, 500 g, was added to the reaction solution, which was separated into layers. The organic layer was washed with water, concentrated, and recrystallized from heptane, obtaining 74 g of 3,3,3-trifluoro-1-(p-toluene-sulfonyloxy)-2-trifluoromethylpropan-2-ol (yield 74%).

Workup

  1. temperaturecooled
  2. customto quench
  3. customthe reaction
  4. customwas separated into layers
  5. washThe organic layer was washed with water
  6. concentrationconcentrated
  7. customrecrystallized from heptane

Sources & evidence

ORD record
ord-b51f56502f3548a4b0248dbdaafd0a3f
Source dataset
uspto-grants-2014_04
Patent number
US08686166B2

Reaction notes

Loading…