Ethyl Bromide → 8-Ethoxy-2,6-dimethyl-nona-2,6-dien

温度

60 °C

THF (500 mL) and sodium hydride (60%, 52 g, 1.3 mol) were charged to a flame dried 2 L reaction flask equipped with a thermometer, a mechanical stirrer, a condenser, and an addition funnel. 8-Hydroxy-2,6-dimethyl-nona-2,6-diene (obtained as detailed above) was added dropwise while allowing the temperature to rise no higher than 50° C. After the addition was completed, the reaction mixture was aged for 1 hour. Ethyl bromide (142 g, 1.3 mol.) was added dropwise for over 2 hours. The reaction mixture was then heated to 60° C. and aged until the conversion rate was shown to be over 90%. The reaction mixture was cooled to lower than 30° C. and quenched by the slow addition of HCl (pH<5, 10%). The layers were split. The aqueous phase was extracted three times with toluene (100 mL). The extracts were added to the crude reaction mixture, which was then washed with saturated sodium bicarbonate 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. Fractional distillation provided the compound 8-ethoxy-2,6-dimethyl-nona-2,6-dien with a boiling point of 125° C. at a pressure of 4.5 mmHg.

1. customdried
2. custom2 L reaction flask
3. customequipped with a thermometer, a mechanical stirrer, a condenser, and an addition funnel
4. customto rise no higher than 50° C
5. additionAfter the addition
6. temperatureThe reaction mixture was cooled to lower than 30° C.
7. customquenched by the slow addition of HCl (pH<5, 10%)
8. customThe layers were split
9. extractionThe aqueous phase was extracted three times with toluene (100 mL)
10. additionThe extracts were added to the crude
11. customreaction mixture, which
12. washwas then washed with saturated sodium bicarbonate
13. dry with materialdried over anhydrous sodium sulphate
14. customThe crude reaction mixture
15. concentrationwas concentrated
16. customThe solvents were recovered via a rotary evaporator
17. distillationFractional distillation

ORDレコード

ord-03640ceaf4204e808df465af3ae8d84c

出典データセット

uspto-grants-2016_09

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US09441185B2