Sodium Hydroxide → (5Z)-3-methylnon-5-en-1-ol

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.

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

ORD record

ord-2ad3ca958f764f2ea07db8b6666c7e3c

Source dataset

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08344023B2