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

Participants

Reaction Conditions

Reaction Steps

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.

Provenance & Evidence