4-Toluenesulfonyl chloride → 4-Toluenesulfonic acid-(2-hydroxy-4-phenyl-2-trifluoromethyl-pentyl)-ester

HRID 1266431Notes

Reaction equation

HRID 1266431 reaction equation
[C:1]1([CH:7]([CH3:17])[CH2:8][C:9]([C:13]([F:16])([F:15])[F:14])([OH:12])[CH2:10][OH:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:18]1([CH3:28])[CH:23]=[CH:22][C:21]([S:24](Cl)(=[O:26])=[O:25])=[CH:20][CH:19]=1>N1C=CC=CC=1>[OH:12][C:9]([C:13]([F:14])([F:15])[F:16])([CH2:8][CH:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[CH3:17])[CH2:10][O:11][S:24]([C:21]1[CH:22]=[CH:23][C:18]([CH3:28])=[CH:19][CH:20]=1)(=[O:26])=[O:25]

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 185512124-Phenyl-2-trifluoromethyl-1,2-pentanediol

Product 1

HCID 185511734-Toluenesulfonic acid-(2-hydroxy-4-phenyl-2-trifluoromethyl-pentyl)-ester

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

4.25 g of 4-phenyl-2-trifluoromethyl-1,2-pentanediol in 30 ml of pyridine is mixed at 0° C. with 3.8 g of 4-toluenesulfonic acid chloride. After 16 hours at 0° C., it is concentrated by evaporation in a vacuum, mixed with ethyl acetate, washed with water, dried (Na2SO4) and concentrated by evaporation. By crystallization from ethyl acetate/hexane, 4.9 g of 4-toluenesulfonic acid-(2-hydroxy-4-phenyl-2-trifluoromethyl-pentyl)ester, melting point 95-96° C., is obtained.

Workup

  1. concentrationit is concentrated by evaporation in a vacuum
  2. additionmixed with ethyl acetate
  3. washwashed with water
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated by evaporation
  6. customBy crystallization from ethyl acetate/hexane, 4.9 g of 4-toluenesulfonic acid-(2-hydroxy-4-phenyl-2-trifluoromethyl-pentyl)ester, melting point 95-96° C.
  7. customis obtained

Sources & evidence

ORD record
ord-bf7df02055c54e91a67400fd4b82c444
Source dataset
uspto-grants-2003_04
Patent number
US06548534B2

Reaction notes

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