(E)-non-2-enoic acid

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

Procedure: To a solution of (E)-ethyl 2-nonenoate in ethanol and 1,4-dioxane was added a 1N aqueous solution of sodium hydroxide. After being stirred at room temperature for 3 hours, the reaction mixture was concentrated and acidified with diluted hydrochloric acid, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, dried over magnesium sulfate and concentrated to give the object compound. the reaction mixture was concentrated the mixture was extracted with ethyl acetate The organic layer was washed with water and brine dried over magnesium sulfate concentrated to give the object compound

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

Procedure: To a solution of (E)-ethyl 2-nonenoate in ethanol and 1,4-dioxane was added a 1N aqueous solution of sodium hydroxide. After being stirred at room temperature for 3 hours, the reaction mixture was concentrated and acidified with diluted hydrochloric acid, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, dried over magnesium sulfate and concentrated to give the object compound. the reaction mixture was concentrated the mixture was extracted with ethyl acetate The organic layer was washed with water and brine dried over magnesium sulfate concentrated to give the object compound

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

Procedure: To a solution of (E)-ethyl 2-nonenoate in ethanol and 1,4-dioxane was added a 1N aqueous solution of sodium hydroxide. After being stirred at room temperature for 3 hours, the reaction mixture was concentrated and acidified with diluted hydrochloric acid, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, dried over magnesium sulfate and concentrated to give the object compound. the reaction mixture was concentrated the mixture was extracted with ethyl acetate The organic layer was washed with water and brine dried over magnesium sulfate concentrated to give the object compound

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

Procedure: A 500 ml flask with a reflux condenser, mechanical stirrer and a dropping funnel, and protected from moisture with a drying tube is charged with LiAlH4 (6.1 g, 0.16 mole) and 200 ml ether. A solution of trans-2-nonenoic acid (7.8 g, 0.05 mole) in 25 ml ether is added at a rate to maintain refluxing. Refluxing is continued for 1 hour and the mixture cooled. Exess reagent is destroyed by the addition of ethyl acetate (5 ml) followed by acidification with 5M HCl. The organic layer is separated, washed with water, dried and distilled under vacuum to give trans-2-nonenol. A 500 ml flask with a reflux condenser, mechanical stirrer and a dropping funnel, and protected from moisture with a drying tube to maintain refluxing Refluxing the mixture cooled Exess reagent is destroyed by the addition of ethyl acetate (5 ml) The organic layer is separated washed with water dried distilled under vacuum

Conditions: temp:130.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Thionyl chloride (131 g, 1.1 mole) is added to trans-2-nonenoic acid (156 g, 1.0 mole). Reaction occurs immediately with the evolution of HCl and SO2. After the initial reaction subsides, the mixture is heated slowly to 130°C. The dark mixture is vacuum distilled to yield trans-2-nonenoyl chloride, b.p. 90°C/2 mm, 155 g, 91% yield. Reaction After the initial reaction subsides distilled

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

Procedure: Malonic acid (342 g, 3.3 mole) is dissolved in 555 ml of dry pyridine (slightly exothermic). The mixture is cooled in ice water and n-heptaldehyde (342 g, 3.0 mole) is added with stirring. After the addition is complete, the ice bath is removed and the mixture allowed to stand at room temperature for 60 hours, and then heated on a steam bath for 8 hours. The reaction mixture is poured onto an equal volume of water. The organic layer is separated, washed with 900 ml 25% HCl, taken up in benzene, washed with water and dried. Distillation under vacuum gave trans-2-nonenoic acid, b.p. 123°C/2 mm, 297 g, 64% yield. After the addition the ice bath is removed heated on a steam bath for 8 hours The reaction mixture is poured onto an equal volume of water The organic layer is separated washed with 900 ml 25% HCl washed with water dried Distillation under vacuum

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

Procedure: To a solution of (E)-ethyl 2-nonenoate in ethanol and 1,4-dioxane was added a 1N aqueous solution of sodium hydroxide. After being stirred at room temperature for 3 hours, the reaction mixture was concentrated and acidified with diluted hydrochloric acid, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, dried over magnesium sulfate and concentrated to give the object compound. the reaction mixture was concentrated the mixture was extracted with ethyl acetate The organic layer was washed with water and brine dried over magnesium sulfate concentrated to give the object compound