Reaktion #53403

Reaktionsgleichung

Pyridine

4-(4-methoxyphenyl)butanol

p-toluenesulfonyl chloride

→

1

Ausbeute 70.1%

4-Methylphenylsulfonic Acid 4-(4-Methoxyphenyl)butyl Ester

Ausbeute 70.1%

Lösungsmittel

chloroform

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGThe reaction mixture was stirred overnight at room temperature
2. 2
   SonstigeAfter this time, the reaction was quenched with 10% HCl (300 mL)
3. 3
   Extraktionextracted with chloroform
4. 4
   WaschenThe organic fraction was washed with saturated NaHCO3, water
5. 5
   Trocknendried over magnesium sulfate
6. 6
   SonstigeThe solvent was removed under reduced pressure
7. 7
   Sonstigethe residue purified by flash chromatography (eluent:hexane/ethyl acetate 15:1)

Vorschrift

Pyridine (15 mL) was added drop wise to a cooled (0° C.) solution of 4-(4-methoxyphenyl)butanol (10.0 g, 0.055 mol) and p-toluenesulfonyl chloride (13.6 g, 0.072 mol) in dry chloroform (100 mL) under stirring. The reaction mixture was stirred overnight at room temperature. After this time, the reaction was quenched with 10% HCl (300 mL) and extracted with chloroform. The organic fraction was washed with saturated NaHCO3, water and dried over magnesium sulfate. The solvent was removed under reduced pressure and the residue purified by flash chromatography (eluent:hexane/ethyl acetate 15:1) to provide 12.9 g (66%) of 1 as clear oil. 1H NMR (360 MHz, CDCl3) δ 1.61 (m, 4H), 2.44 (s, 3H), 2.52 (m, 2H), 3.78 (s, 3H), 4.05 (m, 2H), 6.77 (d, 2H), 7.05 (d, 2H), 7.34 (d, 2H), 7.78 (d, 2H).

Quelle