4-Toluenesulfonyl chloride → (TETRAHYDROFURAN-2,5-DIYL)BIS(METHYLENE) BIS(4-METHYLBENZENESULFONATE)

HRID 8579

Reaktionsgleichung

Reaktionsgleichung von HRID 8579
[OH:1][CH2:2][CH:3]1[CH2:7][CH2:6][CH:5]([CH2:8][OH:9])[O:4]1.[C:10]1([CH3:20])[CH:15]=[CH:14][C:13]([S:16](Cl)(=[O:18])=[O:17])=[CH:12][CH:11]=1>ClCCl.N1C=CC=CC=1>[CH3:20][C:10]1[CH:15]=[CH:14][C:13]([S:16]([O:9][CH2:8][CH:5]2[O:4][CH:3]([CH2:2][O:1][S:16]([C:13]3[CH:14]=[CH:15][C:10]([CH3:20])=[CH:11][CH:12]=3)(=[O:18])=[O:17])[CH2:7][CH2:6]2)(=[O:18])=[O:17])=[CH:12][CH:11]=1

Komponenten

5

Edukt 2

HCID 73974-Toluenesulfonyl chlorideHCID 977922,5-Tetrahydrofurandimethanol

Produkt 1

HCID 259634(TETRAHYDROFURAN-2,5-DIYL)BIS(METHYLENE) BIS(4-METHYLBENZENESULFONATE)

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049PyridineLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

34.0 g (261 mmol) of 2,5-bis(hydroxymethyl)tetrahydrofuran are dissolved in 260 ml of dichloromethane. A solution of 99.0 g (521 mmol) of p-toluenesulfonyl chloride in 52 ml of pyridine and 130 ml of dichloromethane is added dropwise thereto. After stirring at room temperature for 24 hours, the precipitate is filtered off with suction and washed with dichloromethane. The filtrate and the washing phases are combined, washed with dilute hydrochloric acid and then with saturated aqueous sodium bicarbonate solution, dried over magnesium sulfate and evaporated to dryness. The crude product is recrystallized from ethanol.

Aufarbeitung

  1. filtrationthe precipitate is filtered off with suction
  2. washwashed with dichloromethane
  3. washwashed with dilute hydrochloric acid
  4. dry with materialwith saturated aqueous sodium bicarbonate solution, dried over magnesium sulfate
  5. customevaporated to dryness
  6. customThe crude product is recrystallized from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-2b5e20797f2d4f3f95674291e28ba251
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07091198B1

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