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

HRID 2262588Notes

Reaction equation

HRID 2262588 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-b04eed99dfa4403bb7108831a2b17ae5
Source dataset
uspto-grants-2010_12
Patent number
US07851463B2

Reaction notes

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