Reaktion #2146734

Reaktionsgleichung

(5Z)-3-methylnon-5-enyl acetate

sodium hydroxide

→

(5Z)-3-methylnon-5-en-1-ol

Ausbeute 92.0%

Lösungsmittel

ethanol

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe reaction mixture was subsequently heated
2. 2
   Temperaturto reflux for 3 h
3. 3
   TemperaturAfter the reaction mixture had cooled to room temp.
4. 4
   Sonstigethe ethanol was removed in a rotary evaporator under reduced pressure
5. 5
   workup.ADDITIONthe resulting residue diluted with 300 mL of water
6. 6
   ExtraktionThe crude product was extracted twice with 500 mL of ether each, and the combined organic extracts
7. 7
   Waschenwere washed twice with 300 mL of brine
8. 8
   TrocknenAfter drying with sodium sulphate and removal of the solvent under reduced pressure
9. 9
   Sonstigethe resulting residue (51.2 g) was purified by flash chromatography (1.00 kg of silica gel, pentane/ether, 9:1, Rf=0.11)

Vorschrift

In the next step, 55.0 g (278 mmol) of this (5Z)-3-methylnon-5-enyl acetate was dissolved in 600 mL of a 1:1 mixture of ethanol and water. With vigorous stirring, 55.5 g (1.39 mol) of sodium hydroxide was added, and the reaction mixture was subsequently heated to reflux for 3 h. After the reaction mixture had cooled to room temp., the ethanol was removed in a rotary evaporator under reduced pressure, and the resulting residue diluted with 300 mL of water. The crude product was extracted twice with 500 mL of ether each, and the combined organic extracts were washed twice with 300 mL of brine. After drying with sodium sulphate and removal of the solvent under reduced pressure, the resulting residue (51.2 g) was purified by flash chromatography (1.00 kg of silica gel, pentane/ether, 9:1, Rf=0.11) to provide 39.9 g (92%) of (5Z)-3-methylnon-5-en-1-ol as a colourless liquid.

Quelle