4-Toluenesulfonyl chloride → toluene-4-sulfonic acid (S)-2-(3-chlorophenyl)-2-hydroxyethyl ester

HRID 2361138Notes

Reaction equation

HRID 2361138 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@H:8]([OH:11])[CH2:9][OH:10])[CH:5]=[CH:6][CH:7]=1.C(N(CC)CC)C.[S:19](Cl)([C:22]1[CH:28]=[CH:27][C:25]([CH3:26])=[CH:24][CH:23]=1)(=[O:21])=[O:20]>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([C@H:8]([OH:11])[CH2:9][O:10][S:19]([C:22]2[CH:28]=[CH:27][C:25]([CH3:26])=[CH:24][CH:23]=2)(=[O:21])=[O:20])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 10130180(S)-1-(3-Chlorophenyl)ethane-1,2-diol

Product 1

HCID 15442725toluene-4-sulfonic acid (S)-2-(3-chlorophenyl)-2-hydroxyethyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of (S)-1-(3-Chloro-phenyl)-ethane-1,2-diol (9.83 g, 0.057 mol) and triethylamine (11.8 ml, 0.086 mol) a solution of TsCl (10.87 g, 0.057 mol) in dichloromethane (50 mL) was added at 0° C. over 30 min. The mixture was stirred at 0° C. for 4 h. Precipitate formed was removed by filtration, the filtrate was washed with water (50 mL), dried over Na2SO4 and evaporated. The residue was dissolved in CH2Cl2 (200 mL), filtered through a SiO2 pad and evaporated. Colorless oil, 16.34 g (0.050 mol, 88%).

Workup

  1. additionwas added at 0° C. over 30 min
  2. customPrecipitate formed
  3. customwas removed by filtration
  4. washthe filtrate was washed with water (50 mL)
  5. dry with materialdried over Na2SO4
  6. customevaporated
  7. dissolutionThe residue was dissolved in CH2Cl2 (200 mL)
  8. filtrationfiltered through a SiO2 pad
  9. customevaporated

Sources & evidence

ORD record
ord-17155fc687dc43159b7c233df5f4bf42
Source dataset
uspto-grants-2014_04
Patent number
US08686005B2

Reaction notes

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