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

HRID 390295Notes

Reaction equation

HRID 390295 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 were 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 was 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 was evaporated under reduced pressure

Sources & evidence

ORD record
ord-fe885961caa949f495f27dbdd7bc6379
Source dataset
uspto-grants-2013_02
Patent number
US08383641B2

Reaction notes

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