4-Toluenesulfonyl chloride → 2-(4-Chlorophenoxy)ethyl 4-methylbenzene-1-sulfonate

HRID 1928540Notes

Reaction equation

HRID 1928540 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([O:6][CH2:7][CH2:8][OH:9])=[CH:4][CH:3]=1.CCN(CC)CC.[CH3:19][C:20]1[CH:25]=[CH:24][C:23]([S:26](Cl)(=[O:28])=[O:27])=[CH:22][CH:21]=1>C(Cl)Cl>[CH3:19][C:20]1[CH:25]=[CH:24][C:23]([S:26]([O:9][CH2:8][CH2:7][O:6][C:5]2[CH:10]=[CH:11][C:2]([Cl:1])=[CH:3][CH:4]=2)(=[O:28])=[O:27])=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 159072-(4-Chlorophenoxy)ethanol

Product 1

HCID 107349442-(4-Chlorophenoxy)ethyl 4-methylbenzene-1-sulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(4-chlorophenoxy)ethanol (2.0 g, 11.6 mmol) in DCM (10 mL) was added Et3N (5 mL) and 4-methylbenzene-1-sulfonyl chloride (TsCl; 2.43 g, 12.8 mmol) sequentially. The reaction mixture was stirred at room temperature overnight and partitioned between water and ethyl acetate. The organic layer was washed with water, 5% sodium bicarbonate (NaHCO3), and brine and concentrated. The resulting residue was washed with hexane to afford the title compound quantitatively.

Workup

  1. custompartitioned between water and ethyl acetate
  2. washThe organic layer was washed with water, 5% sodium bicarbonate (NaHCO3), and brine
  3. concentrationconcentrated
  4. washThe resulting residue was washed with hexane

Sources & evidence

ORD record
ord-16e797c706f9466ca6e26a437581edac
Source dataset
uspto-grants-2012_05
Patent number
US08183374B2

Reaction notes

Loading…