Thionyl Chloride → 4-Hydroxybenzene-1-sulfonyl chloride

HRID 722451Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 722451
S(Cl)([Cl:3])=O.[Na+].[OH:6][C:7]1[CH:12]=[CH:11][C:10]([S:13]([O-:16])(=O)=[O:14])=[CH:9][CH:8]=1>C(Cl)Cl.CN(C=O)C>[OH:6][C:7]1[CH:12]=[CH:11][C:10]([S:13]([Cl:3])(=[O:16])=[O:14])=[CH:9][CH:8]=1

Komponenten

5

Edukt 2

HCID 24386Thionyl ChlorideHCID 4379756Sodium 4-hydroxybenzenesulfonate

Produkt 1

HCID 114240934-Hydroxybenzene-1-sulfonyl chlorideAusbeute 98,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideKatalysatorHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

A solution of 31.4 ml (430 mmol) of thionyl chloride and 0.2 ml (2.58 mmol) of DMF was quickly added to 10 g (43 mmol) of 4-hydroxybenzenesulfonic acid sodium salt under N2 atmosphere. The resulting mixture is stirred at 65° C. for 6 h. At the end of this time, the mobile, nearly homogenous reaction mixture is poured on ice with vigorous stirring. An oily lower layer is produced and which is dissolved in 100 ml of CH2Cl2. The aqueous layer is extracted with CH2Cl2 and the combined organic solution is dried over MgSO4 and concentrated under reduced pressure to give 8.19 g of 4-hydroxybenzenesulfonyl chloride; NMR (CDCl3): 5.3 (br s, 1H), 7.01 (d, 2H, J=9.08 Hz), 7.94 (d, 2H, J=9.08 Hz).

Aufarbeitung

  1. additionAt the end of this time, the mobile, nearly homogenous reaction mixture is poured on ice with vigorous stirring
  2. customAn oily lower layer is produced
  3. extractionThe aqueous layer is extracted with CH2Cl2
  4. dry with materialthe combined organic solution is dried over MgSO4
  5. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-c2302c81c6544f9ea17489e21660dc2a
Quelldatensatz
uspto-grants-2006_11
Patentnummer
US07138432B1

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