2-Chloroethanol → Ethanol, 2-chloro-, 1-(4-methylbenzenesulfonate)

HRID 85120

Reaction equation

HRID 85120 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[Cl:12][CH2:13][CH2:14][OH:15]>N1C=CC=CC=1>[CH3:11][C:1]1[CH:6]=[CH:5][C:4]([S:7]([O:15][CH2:14][CH2:13][Cl:12])(=[O:9])=[O:8])=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 342-ChloroethanolHCID 73974-Toluenesulfonyl chloride

Product 1

HCID 6639Ethanol, 2-chloro-, 1-(4-methylbenzenesulfonate)Yield 88.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
2.5 °C

Procedure

In a typical run, p-toluenesulfonyl chloride (TsCl, 70.5 g, 0.37 mol) was added slowly to a solution of 2-chloroethanol (38; 25.0 g, 0.31 mol) in pyridine (100 mL) at 0° C. The reaction mixture was stirred at 0-5° C. for 18 h. Ice water (300 mL) was added and the resulting mixture was extracted with ethyl acetate (3×100 mL). The combined organic layers were washed with 1 N HCl (3×100 mL), water (100 mL×3), dried (Na2SO4) and concentrated under reduced pressure to afford 2-chloroethyl 4-methylbenzenesulfonate 39 (64.3 g, 88%).

Workup

  1. extractionthe resulting mixture was extracted with ethyl acetate (3×100 mL)
  2. washThe combined organic layers were washed with 1 N HCl (3×100 mL), water (100 mL×3)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8d9e6a3f48bc427483e6475ed283561b
Source dataset
uspto-grants-2014_09
Patent number
US08846947B2

Linked notes

Loading…