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

HRID 655596

Reaction equation

HRID 655596 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-528080843ae94db9a26863170ea3e0c3
Source dataset
uspto-grants-2011_12
Patent number
US08071602B2

Linked notes

Loading…