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

HRID 655596

Reaktionsgleichung

Reaktionsgleichung von HRID 655596
[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

Komponenten

5

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-528080843ae94db9a26863170ea3e0c3
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08071602B2

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