Reaktion #76382

Reaktionsgleichung

(4-pentyl-cyclohexyl)-methanol

(4-Pentyl-cyclohexyl)-methanol

potassium carbonate

sodium periodate

2-Propanol

→

4-pentyl-cyclohexanecarboxaldehyde

Ausbeute 83.0%

4-Pentyl-cyclohexanecarboxaldehyde

Ausbeute 83.0%

Lösungsmittel

chloroform water

ruthenium chloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe reaction mixture was stirred for another 30 min at 60 C
2. 2
   Filtrationfiltered through celite
3. 3
   Extraktionextracted with dichloromethane
4. 4
   Trocknendried over MgSO4
5. 5
   Einengenconcentrated in vacuo
6. 6
   SonstigePurification by chromatography on silica gel (dichloromethane)

Vorschrift

To a slurry of (4-pentyl-cyclohexyl)-methanol (21) (1 equi.), benzyltriethylammonium chloride (0.05 equi.), potassium carbonate (0.15 equi.), and sodium periodate (1.5 equi.) in chloroform-water (1:1) (2 mL/mmole), ruthenium chloride (0.03 equi.) was added at room temperature. The reaction mixture was stirred at 60 C for 2 h. 2-Propanol (0.3 equi.) was added and the reaction mixture was stirred for another 30 min at 60 C, cooled to room temperature, filtered through celite, extracted with dichloromethane, dried over MgSO4, and concentrated in vacuo. Purification by chromatography on silica gel (dichloromethane) afforded 4-pentyl-cyclohexanecarboxaldehyde (22) as a colorless oil (83%).

Quelle