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

HRID 1590527

Reaktionsgleichung

Reaktionsgleichung von HRID 1590527
[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>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

4

Edukt 2

HCID 7369Benzenesulfonyl chlorideHCID 175704,4'-Thiodiphenol

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

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

Quellen und Nachweise

ORD-Eintrag
ord-5c3c5df52ce8437a8d1fbd6943476805
Quelldatensatz
uspto-grants-1993_04
Patentnummer
US05204011

Verknüpfte Notizen

Wird geladen…