تفاعل #2146734

معادلة التفاعل

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

sodium hydroxide

→

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

المردود 92.0%

المذيبات

ethanol

water

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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.

المصدر