Dimethylformamide → (E)-Dodec-8-enyl acetate

Temperature

110 °C

Z/E-8-dodecenyl bromide (520 mg, 2.2 mmol), prepared as described above, was weighed into a 50 mL round bottom flask with a magnetic stir bar. Sodium acetate (540 mg, 6.6 mmol), freshly fused, was added in a single portion, followed by dimethyl formamide (5 mL). The flask was equipped with a condenser and was placed in a preheated oil bath (55° C.). The oil bath was further heated to 110° C. over 3 hours. The progress of the reaction was monitored by thin layer chromatography (TLC) using hexane:ethyl acetate in a ratio of 9:1 as the eluant. After 5 hours the reaction mixture was removed from the heat and allowed to cool to ambient temperature. Water (10 mL) was added to dilute the reaction mixture, and the resulting aqueous phase was extracted with hexane (3×15 mL). The combined hexane extracts were washed with water (2×10 mL) and brine (10 mL). The resulting organic phase was dried over Na2SO4, filtered, and the solvent evaporated under reduced pressure to yield the Z/E-8-dodecenyl acetate product as a clear liquid (360 mg, 73%). The Z/E ratio was determined to be 92:8 by gas chromatography (GC) using a DB-XLB column.

1. customwas weighed into a 50 mL round bottom flask with a magnetic stir bar
2. additionwas added in a single portion
3. customThe flask was equipped with a condenser
4. customwas placed in a preheated oil bath
5. custom(55° C.)
6. customAfter 5 hours the reaction mixture was removed from the
7. temperatureheat
8. temperatureto cool to ambient temperature
9. additionWater (10 mL) was added
10. additionto dilute the reaction mixture
11. extractionthe resulting aqueous phase was extracted with hexane (3×15 mL)
12. washThe combined hexane extracts were washed with water (2×10 mL) and brine (10 mL)
13. dry with materialThe resulting organic phase was dried over Na2SO4
14. filtrationfiltered
15. customthe solvent evaporated under reduced pressure

ORD record

ord-eb4b148cfe7343ad9a72556bbb4cb95a

Source dataset

uspto-grants-2005_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06838576B1