[(10E,12E)-tetradeca-10,12-dienyl] acetate

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

Procedure: The 2.4 g of tetradecadienol was dissolved in 55 ml of pentane containing 30 μl of thiophenol in a 100-ml round bottom flask. The flask was heated with a water bath, and the pentane was distilled off. Then a reflux condenser was connected to the flask, and the mixture was heated at 100° C. for 2 hours. The residue was dissolved in 600 ml of heptane which was removed by a rotary evaporator. The thiophenol was removed simultaneously. The yield of isomerized tetradecadienol was 2.01 g (84%). The isomer content by GC analysis was 62% EE, 19% EZ, 15% ZE, 4% ZZ. The tetradecadienol was recrystallized twice at low temperature from pentane to give 0.83 g of a product of 96.2% EE. 10,12-Tetradecadienol in 75 ml pyridine and 5 ml acetic anhydride was refluxed 1.5 hours. After the solution was cooled, 200 ml hexane was added, and the mixture was extracted successively with water, 6N hydrochloric acid (twice), and water. The pentane phase was dried over sodium sulfate, filtered, and the pentane was removed by rotary evaporation, leaving crude product, which was purified by silica gel liquid chromatography (elution in 10% ether/hexane); the yield was 1.0 g (94% based on the alcohol). After the solution was cooled the mixture was extracted successively with water, 6N hydrochloric acid (twice), and water The pentane phase was dried over sodium sulfate filtered the pentane was removed by rotary evaporation leaving crude product, which was purified by silica gel liquid chromatography (elution in 10% ether/hexane)

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

Procedure: To prepare (E,E)-10,12-tetradecadien-1-ol acetate (I), the tetradecadiene (D) (5.6 g) in 200 ml methanol containing eight drops concentrated HCl was refluxed for 15 minutes. After the solution was cooled, 400 ml of water was added, and the mixture was extracted three times with hexane. The hexane extract was dried over sodium sulfate, and the hexane was removed with a rotary evaporator leaving 3 g crude 10,12-tetradecadienol, which was purified by silica gel liquid chromatography. Unwanted side products were eluted with 10% ether/hexane, and the alcohol was eluted with 50% ether/hexane, giving 2.4 g (66% yield based on the dodecenenitrile (B)). After the solution was cooled the mixture was extracted three times with hexane The hexane extract was dried over sodium sulfate the hexane was removed with a rotary evaporator

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

Procedure: To prepare (E,E)-10,12-tetradecadien-1-ol acetate (I), the tetradecadiene (D) (5.6 g) in 200 ml methanol containing eight drops concentrated HCl was refluxed for 15 minutes. After the solution was cooled, 400 ml of water was added, and the mixture was extracted three times with hexane. The hexane extract was dried over sodium sulfate, and the hexane was removed with a rotary evaporator leaving 3 g crude 10,12-tetradecadienol, which was purified by silica gel liquid chromatography. Unwanted side products were eluted with 10% ether/hexane, and the alcohol was eluted with 50% ether/hexane, giving 2.4 g (66% yield based on the dodecenenitrile (B)). After the solution was cooled the mixture was extracted three times with hexane The hexane extract was dried over sodium sulfate the hexane was removed with a rotary evaporator

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

Procedure: To prepare (E,E)-10,12-tetradecadien-1-ol acetate (I), the tetradecadiene (D) (5.6 g) in 200 ml methanol containing eight drops concentrated HCl was refluxed for 15 minutes. After the solution was cooled, 400 ml of water was added, and the mixture was extracted three times with hexane. The hexane extract was dried over sodium sulfate, and the hexane was removed with a rotary evaporator leaving 3 g crude 10,12-tetradecadienol, which was purified by silica gel liquid chromatography. Unwanted side products were eluted with 10% ether/hexane, and the alcohol was eluted with 50% ether/hexane, giving 2.4 g (66% yield based on the dodecenenitrile (B)). After the solution was cooled the mixture was extracted three times with hexane The hexane extract was dried over sodium sulfate the hexane was removed with a rotary evaporator