Potassium Carbonate → 9-Tetradecenyl formate

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Three fields of cotton in a late fruiting stage were used to evaluate the effectiveness of tetradecenyl formate in controlling Heliothis species. In this case, the 9-tetradecenyl formate was prepared from 9-tetradecenyl acetate rather than directly from 9-decenyl formate. In a typical process 21.1 g (0.08 mol) of tetradecenyl acetate, 22.2 g (0.16 mol) K2CO3, 200 mL methanol, and 2 mL water were added to a 500 mL one neck round bottom flask. The mixture was stirred for two hours at room temperature. Then 200 mL of diethyl ether was added, and the mixture was filtered. The ether layer was washed with water, then saturated NaCl solution, then dried over MgSO4. The dried solution was filtered and concentrated on a rotary evaporator. The product consisting of 9-tetradecenyl alcohol was then reacted with formic acid in benzene at gentle reflux (~80° C.) for 24 hours. Then additional formic acid was added and the gentle reflux continued for another 24 hours. The 9 -tetradecenyl formate was recovered by extraction.

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