4-Toluenesulfonyl chloride → Toluene-4-sulfonic acid (S)-2-phenyl-propyl ester

HRID 2357000Notes

Reaction equation

HRID 2357000 reaction equation
[C:1]1([C@H:7]([CH3:10])[CH2:8][OH:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:11]1([CH3:21])[CH:16]=[CH:15][C:14]([S:17](Cl)(=[O:19])=[O:18])=[CH:13][CH:12]=1>ClCCl>[C:1]1([C@H:7]([CH3:10])[CH2:8][O:9][S:17]([C:14]2[CH:15]=[CH:16][C:11]([CH3:21])=[CH:12][CH:13]=2)(=[O:19])=[O:18])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 4476612-Phenylpropanol

Product 1

HCID 13791931Toluene-4-sulfonic acid (S)-2-phenyl-propyl esterYield 100.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 20 g of (S)-(−)-2-phenyl-1-propanol in 240 ml of dichloromethane was added in portions 28 g of p-toluenesulfonyl chloride (146.8 mmol). After stirring for 18 h at room temperature, the organic phase was washed with 100 ml of water, dried over magnesium sulfate, filtered, and the solvent evaporated under reduced pressure to yield 43 g of the title compound.

Workup

  1. washthe organic phase was washed with 100 ml of water
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-8b04e68b00234eb4af708efb9d4c43a2
Source dataset
uspto-grants-2010_07
Patent number
US07759397B2

Reaction notes

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