Реакция #2146734

Уравнение реакции

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

sodium hydroxide

→

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

Выход 92.0%

Растворители

ethanol

water

Условия реакции

Обработка

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

Методика

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.

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