Benzenesulfonyl chloride → Bis[4-(benzenesulfonyloxy)phenyl] Sulfide

HRID 1742557

Reaktionsgleichung

Reaktionsgleichung von HRID 1742557
[S:1]([C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[C:16]1([S:22](Cl)(=[O:24])=[O:23])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CN(C)C1C=CN=CC=1.N1C=CC=CC=1>[C:16]1([S:22]([O:8][C:5]2[CH:6]=[CH:7][C:2]([S:1][C:9]3[CH:14]=[CH:13][C:12]([O:15][S:22]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)(=[O:24])=[O:23])=[CH:11][CH:10]=3)=[CH:3][CH:4]=2)(=[O:24])=[O:23])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Komponenten

5

Edukt 2

HCID 7369Benzenesulfonyl chlorideHCID 175704,4'-Thiodiphenol

Produkt 1

HCID 11841360Bis[4-(benzenesulfonyloxy)phenyl] SulfideAusbeute 98 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 1049PyridineLösungsmittel

Versuchsvorschrift

A 100 ml 3-necked oven-dried flask is equipped with a magnetic stirring bar and a CaCl2 -Drierite drying tube and is charged with 4,4'-thiodiphenol (5.3 grams, 24.3 mmol), benzenesulfonyl chloride (6.5 ml, 50.9 mmol), 4-dimethylaminopyridine (0.59 grams, 4.8 mmol), and anhydrous pyridine (40 ml). The mixture is stirred at ambient temperature for 18 hours, and at reflux for 4 hours, then is poured into ice-cold water (100 ml) with vigorous stirring, and the yellow oil that separates is extracted into CH2Cl2 (100 ml), and washed with water (100 ml). Drying (MgSO4), filtration and concentration affords a yellow oil. Purification by filtration through a column packed with flash-grade silica gel (5"×2" i.d.), eluting with CH2Cl2 (ca. 0.5 1), gives after solvent removal under vacuum 11.8 grams (98 percent yield) of the title compound as a faintly yellowish, thick glass material.

Aufarbeitung

  1. customA 100 ml 3-necked oven-dried flask is equipped with a magnetic stirring bar and a CaCl2 -Drierite drying tube
  2. temperatureat reflux for 4 hours
  3. extractionthe yellow oil that separates is extracted into CH2Cl2 (100 ml)
  4. washwashed with water (100 ml)
  5. customDrying
  6. filtration(MgSO4), filtration and concentration
  7. customaffords a yellow oil
  8. customPurification
  9. filtrationby filtration through a column
  10. washeluting with CH2Cl2 (ca. 0.5 1)
  11. customgives

Quellen und Nachweise

ORD-Eintrag
ord-5ea9559c3c394944b48d528ed0e455f4
Quelldatensatz
uspto-grants-1994_08
Patentnummer
US05340489

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