반응 #2146734

반응 방정식

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

sodium hydroxide

→

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

수율 92.0%

용매

ethanol

water

반응 조건

후처리

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

실험 절차

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.

출처