Sulfuric Acid → 4,4,5,5,5-Pentafluoropentyl 4-methylbenzenesulfonate

HRID 1440970Notes

Reaction equation

HRID 1440970 reaction equation
[F:1][C:2]([F:11])([C:7]([F:10])([F:9])[F:8])[CH2:3][CH2:4][CH2:5][OH:6].[S:12](Cl)([C:15]1[CH:21]=[CH:20][C:18]([CH3:19])=[CH:17][CH:16]=1)(=[O:14])=[O:13].S(=O)(=O)(O)O>N1C=CC=CC=1>[F:1][C:2]([F:11])([C:7]([F:8])([F:9])[F:10])[CH2:3][CH2:4][CH2:5][O:6][S:12]([C:15]1[CH:21]=[CH:20][C:18]([CH3:19])=[CH:17][CH:16]=1)(=[O:14])=[O:13]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 73974-Toluenesulfonyl chlorideHCID 5479674,4,5,5,5-Pentafluoropentan-1-ol

Product 1

HCID 220330274,4,5,5,5-Pentafluoropentyl 4-methylbenzenesulfonateYield 101.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 17.3 g of 4,4,5,5,5-pentafluoropentanol in 40 ml of pyridine is mixed at 0° C. with 21 g of tosyl chloride and stirred for 3 hours at 0° C. For working up, the reaction mixture is added to 2 n sulfuric acid, extracted with diethyl ether, washed neutral with water, dried on sodium sulfate and concentrated by evaporation in a vacuum. 32.7 g of crude toluene-4-sulfonic acid-4,4,5,5,5-pentafluoropentyl ester is obtained as oil. The latter is dissolved in 300 ml of acetone and refluxed with 23 g of potassium thioacetate for 18 hours at 100° C. bath temperature. Then, it is mixed with water, extracted with diethyl ether, washed with water, dried on sodium sulfate, concentrated by evaporation in a vacuum and distilled. At 173°-177° C., 15 g of thioacetic acid-S-(4,4,5,5,5-pentafluoropentyl)-ester is obtained.

Workup

  1. extractionextracted with diethyl ether
  2. washwashed neutral with water
  3. customdried on sodium sulfate
  4. concentrationconcentrated by evaporation in a vacuum

Sources & evidence

ORD record
ord-2229528fc9a64cf7ae578a04748965bd
Source dataset
uspto-grants-1996_03
Patent number
US05502046

Reaction notes

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