3,7-Dimethylocta-2,6-Dienal → 4,8-Dimethylnona-3,7-dien-2-ol

Temperature

30 °C

Methyl lithium in tetrahydrofuran (THF) (1.6 L, 1 M) was charged to a flame dried 3 L reaction flask equipped with a thermometer, a mechanical stirrer, condenser, and an addition funnel. Citral was added dropwise for over 2-2.5 hours. The reaction mixture was aged until the conversion rate was greater than 90%. The reaction mixture was cooled to lower than 30° C. and quenched by the slow addition of HCl (pH<5.10%). The aqueous phase was extracted three times with toluene (100 mL) and the extracts were added to the crude reaction mixture. The crude reaction mixture was then washed with saturated sodium bicarbonate (500 mL) followed by saturated salt solution and dried over anhydrous sodium sulphate. The crude reaction mixture was concentrated. The solvents were recovered via a rotary evaporator to provide 8-hydroxy-2,6-dimethyl-nona-2,6-diene.

1. customdried
2. custom3 L reaction flask
3. customequipped with a thermometer, a mechanical stirrer, condenser, and an addition funnel
4. customquenched by the slow addition of HCl (pH<5.10%)
5. extractionThe aqueous phase was extracted three times with toluene (100 mL)
6. additionthe extracts were added to the crude
7. customreaction mixture
8. customThe crude reaction mixture
9. washwas then washed with saturated sodium bicarbonate (500 mL)
10. dry with materialdried over anhydrous sodium sulphate
11. customThe crude reaction mixture
12. concentrationwas concentrated
13. customThe solvents were recovered via a rotary evaporator

ORD record

ord-83aeca3a6a51447a989c36bbe775b2b3

Source dataset

uspto-grants-2016_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09441185B2