[(Z)-tetradec-9-enyl] acetate

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A process for preparing 9-tetradecenyl formate by reacting 1-hexene or 5-decene with 9-decenyl acetate in accordance with the method of claim 7 to obtain 9-tetradecenyl acetate, then reacting the acetate with water to obtain the corresponding alcohol and then reacting the alcohol with formic acid to obtain the formate.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 2/1 trans to cis ratio of 9-tetradecenal was evaluated in the same manner as was used in the preceding example. The 9-tetradecenal was prepared from 9-tetradecenyl alcohol prepared in the same manner as described in the preceding example. About 21 grams of the alcohol in a 50/50 weight ratio selection of dichloromethane was added dropwise to a flask charged with 43 g (0.2 mol) pyridinium chlorochromate, 20 g celite and 200 mL dichloromethane. The mixture was stirred at room temperature for about 2 hours after addition of the alcohol solution was complete. Then 200 mL of hexane was added and the mixture was filtered. The solvent was evaporated and the product vacuum distilled through a 2 ft.×3/4 in. packed column (Penn State stainless steel packing). A 36% yield of pure 9-tetradecenyl acetate was obtained. prepared in the same manner the mixture was filtered The solvent was evaporated the product vacuum distilled through a 2 ft.×3/4 in

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 2/1 trans to cis ratio of 9-tetradecenal was evaluated in the same manner as was used in the preceding example. The 9-tetradecenal was prepared from 9-tetradecenyl alcohol prepared in the same manner as described in the preceding example. About 21 grams of the alcohol in a 50/50 weight ratio selection of dichloromethane was added dropwise to a flask charged with 43 g (0.2 mol) pyridinium chlorochromate, 20 g celite and 200 mL dichloromethane. The mixture was stirred at room temperature for about 2 hours after addition of the alcohol solution was complete. Then 200 mL of hexane was added and the mixture was filtered. The solvent was evaporated and the product vacuum distilled through a 2 ft.×3/4 in. packed column (Penn State stainless steel packing). A 36% yield of pure 9-tetradecenyl acetate was obtained. prepared in the same manner the mixture was filtered The solvent was evaporated the product vacuum distilled through a 2 ft.×3/4 in

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 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. the mixture was filtered The ether layer was washed with water saturated NaCl solution, then dried over MgSO4 The dried solution was filtered concentrated on a rotary evaporator was then reacted with formic acid in benzene at gentle reflux (~80° C.) for 24 hours the gentle reflux continued for another 24 hours The 9 -tetradecenyl formate was recovered by extraction

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A process for preparing 9-tetradecenyl formate by reacting 1-hexene or 5-decene with 9-decenyl acetate in accordance with the method of claim 7 to obtain 9-tetradecenyl acetate, then reacting the acetate with water to obtain the corresponding alcohol and then reacting the alcohol with formic acid to obtain the formate.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 2/1 trans to cis ratio of 9-tetradecenal was evaluated in the same manner as was used in the preceding example. The 9-tetradecenal was prepared from 9-tetradecenyl alcohol prepared in the same manner as described in the preceding example. About 21 grams of the alcohol in a 50/50 weight ratio selection of dichloromethane was added dropwise to a flask charged with 43 g (0.2 mol) pyridinium chlorochromate, 20 g celite and 200 mL dichloromethane. The mixture was stirred at room temperature for about 2 hours after addition of the alcohol solution was complete. Then 200 mL of hexane was added and the mixture was filtered. The solvent was evaporated and the product vacuum distilled through a 2 ft.×3/4 in. packed column (Penn State stainless steel packing). A 36% yield of pure 9-tetradecenyl acetate was obtained. prepared in the same manner the mixture was filtered The solvent was evaporated the product vacuum distilled through a 2 ft.×3/4 in

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 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. the mixture was filtered The ether layer was washed with water saturated NaCl solution, then dried over MgSO4 The dried solution was filtered concentrated on a rotary evaporator was then reacted with formic acid in benzene at gentle reflux (~80° C.) for 24 hours the gentle reflux continued for another 24 hours The 9 -tetradecenyl formate was recovered by extraction