4-Toluenesulfonyl chloride → (S)-Toluene-4-sulfonic acid 3-hydroxybutyl ester

HRID 1005585Notes

Reaction equation

HRID 1005585 reaction equation
[CH2:1]([OH:6])[CH2:2][C@@H:3]([OH:5])[CH3:4].C(N(CC)CC)C.[C:14]1([CH3:24])[CH:19]=[CH:18][C:17]([S:20](Cl)(=[O:22])=[O:21])=[CH:16][CH:15]=1>ClCCl>[C:14]1([CH3:24])[CH:19]=[CH:18][C:17]([S:20]([O:6][CH2:1][CH2:2][C@@H:3]([OH:5])[CH3:4])(=[O:22])=[O:21])=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 446973(+)-1,3-Butanediol

Product 1

HCID 13204325(S)-Toluene-4-sulfonic acid 3-hydroxybutyl esterYield 83.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of (S)-1,3-butanediol (1.0 g) and triethylamine (1.12 g) in dichloromethane (30 ml) was added portionwise p-toluenesulfonyl chloride (2.12 g) at 0° C., and then the mixture was stirred at ambient temperature for 3hours and stand overnight. The resulting solution was dilueted with dichloromethane (30 ml) and the organic layer was washed successively with 1 N hydrochloric acid, saturated sodium bicarbonate aqueous solution and brine. Drying, filtering and removal of solvents afforded (S)-3-hyrdoxybutyl p-toluenesulfonate (2.26 g).

Workup

  1. waitstand overnight
  2. washthe organic layer was washed successively with 1 N hydrochloric acid, saturated sodium bicarbonate aqueous solution and brine
  3. customDrying
  4. filtrationfiltering
  5. customremoval of solvents

Sources & evidence

ORD record
ord-0f7552a6ee504d0bb19371178ff9fad3
Source dataset
uspto-grants-2000_04
Patent number
US06054457

Reaction notes

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