4-Toluenesulfonyl chloride → 1-Tosyloxy-3-(3-methoxyphenyl)propane

HRID 2290936Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2290936
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][CH2:11][OH:12])[CH:6]=[CH:7][CH:8]=1.[C:13]1([CH3:23])[CH:18]=[CH:17][C:16]([S:19](Cl)(=[O:21])=[O:20])=[CH:15][CH:14]=1>N1C=CC=CC=1>[S:19]([O:12][CH2:11][CH2:10][CH2:9][C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=1)([C:16]1[CH:17]=[CH:18][C:13]([CH3:23])=[CH:14][CH:15]=1)(=[O:21])=[O:20]

Komponenten

4

Edukt 2

HCID 73974-Toluenesulfonyl chlorideHCID 961303-m-Anisyl-1-propanol

Produkt 1

HCID 5904971-Tosyloxy-3-(3-methoxyphenyl)propaneAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

A solution of 3-(3-methoxyphenyl)-propanol (69 g, 0.42 mole) and pyridine (400 mL) was stirred at 5° C. as p-toluenesulfonyl chloride (87 g, 0.46 mole) was added portionwise. The reaction mixture was stirred at room temperature for 2 hours, then was poured onto ice/concentrated HCl and was extracted with ether. The extracts were washed with 2N HCl, wawter, saturated aqueous NaCl, dried (MgSO4), filtered, and evaporated to yield 126 g yellow oil, (95%); M+ 320.

Aufarbeitung

  1. additionwas added portionwise
  2. additionwas poured onto ice/concentrated HCl
  3. extractionwas extracted with ether
  4. washThe extracts were washed with 2N HCl, wawter, saturated aqueous NaCl
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-4f25fc0fd6dd493fabbdbd0997ac2a6f
Quelldatensatz
uspto-grants-1986_10
Patentnummer
US04618683

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