反応 #2146734

反応方程式

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

sodium hydroxide

→

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

収率 92.0%

溶媒

ethanol

water

反応条件

後処理

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

実験手順

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.

出典