Reaktion #49759

Reaktionsgleichung

Cyclopentanol

p-toluenesulfonyl chloride

potassium hydroxide

→

cyclopentyl p-toluenesulfonate

Ausbeute 81.8%

Lösungsmittel

ether

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.DISSOLUTIONdissolved
2. 2
   Temperaturwhile cooling below 10° C. in a water bath
3. 3
   workup.ADDITIONAfter addition
4. 4
   SonstigeAfter completion of the reaction
5. 5
   Sonstigethe organic layer and the aqueous layer were separated
6. 6
   SonstigeThe organic layer was dried
7. 7
   Einengenconcentrated under reduced pressure

Vorschrift

Cyclopentanol (10 g, 0.116 mol), p-toluenesulfonyl chloride (24.8 g, 0.128 mol) and ether (100 ml) were charged into a 200 cc round-bottom flask and dissolved. Then, potassium hydroxide (32.5 g, 0.58 mol) in a powder form was added slowly thereto while cooling below 10° C. in a water bath. After addition, the mixture was stirred as it was for additional 2 hours. After completion of the reaction, the mixture was poured into ice-water (20 ml), and the organic layer and the aqueous layer were separated. The organic layer was dried, and concentrated under reduced pressure to obtain cyclopentyl p-toluenesulfonate as a pale yellow viscous liquid (22.0 g, 81.8% yield).

Quelle