(E)-non-2-en-1-ol

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

Procedure: Pyridine (100 ml) and trans-2-nonen-1-ol (28.4 g, 0.2 mole) are heated to 110°C and acetic anhydride (30.6 g, 0.3 mole) is added dropwise. The reaction mixture is maintained at 110°-115° for 2 hours and 120°-125°C for 3 hours. The mixture is cooled and washed with water, 5% sulfuric acid, and finally water. The solution is dried over sodium sulfate. Trans-2-nonenyl acetate, 33.0 g is obtained by vacuum distillation, b.p. 70°-5°C/50-55 mm. The reaction mixture is maintained at 110°-115° for 2 hours and 120°-125°C for 3 hours The mixture is cooled washed with water, 5% sulfuric acid, and finally water The solution is dried over sodium sulfate

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Acetyl formate (39.6 g, 0.45 mole) is added dropwise to a cooled mixture of sodium formate (6.8 g, 0.10 mole) and trans-2-nonen-1-ol (47.3 g, 0.33 mole). When the addition is complete, the reaction mixture temperature is maintained at 60°C for 7 hours. The mixture is cooled and diluted with water. The organic layer is separated and washed with 5% sodium bicarbonate, water and then dried over sodium sulfate. Trans-2-nonenyl formate, 419 g is obtained on distillation, b.p. 60°-5°C/50-55 mm. When the addition The mixture is cooled The organic layer is separated washed with 5% sodium bicarbonate, water dried over sodium sulfate

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

Procedure: To a flask equipped with a reflux condenser, mechanical stirrer and dropping funnel is added trans-2-nonenol (14.2 g, 0.1 mole), N1N-dimethylaniline (12 g, 0.1 mole) and 20 ml ether. To the stirred mixture is added dropwise phenylacetyl chloride (15.5 g, 0.1 mole) at a rate to maintain a vigorous reflux of ether. After the addition, the mixture is warmed on a water bath for 2 hours and then allowed to stand several hours. The ether layer is separated from the precipitate and extracted with 10% sulfuric acid. The ether layer is dried over anhydrous sodium sulfide and purified up to give trans-2-nonenyl phenylacetate. To a flask equipped with a reflux condenser, mechanical stirrer to maintain After the addition the mixture is warmed on a water bath for 2 hours to stand several hours The ether layer is separated from the precipitate extracted with 10% sulfuric acid The ether layer is dried over anhydrous sodium sulfide purified up

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

Procedure: Isobutyric acid (22.0 g, 0.25 mole), trans-2-nonen-1-ol (44.3 g, 0.25 mole), xylene (100 ml) and p-toluenesulfonic acid are heated to 145°C. The solution is refluxed for 5 minutes and 4.5 ml water is collected by distillation. The reaction mixture is cooled and first washed with water followed by 5% sodium carbonate. The washed solution is dried over sodium sulfate and distilled to yield 34.1 g of trans-2-nonenyl isobutyrate, b.p. 87° - 88°C/0.5 mm. An analytical sample is obtained for taste evaluation using gas chromatography. The solution is refluxed for 5 minutes 4.5 ml water is collected by distillation The reaction mixture is cooled first washed with water The washed solution is dried over sodium sulfate distilled

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

Procedure: Trans-2-nonenal (7.0 g, 0.05 mole) is dissolved in 50 ml of ether and added to a solution of LiAlH4 (0.54 g, 0.014 mole) in 50 ml of ether at such a rate to maintain gentle refluxing. When the addition is complete, the solution is refluxed for one hour. Ethyl acetate (2 ml) is added to destroy excess LiAlH4. The mixture is acidified with 5M HCl. The ether layer is separated, washed 2X with water, and dried over sodium sulfate. The ether solution is concentrated and the residue vacuum distilled to yield trans-2-nonenol. to maintain gentle refluxing When the addition the solution is refluxed for one hour to destroy excess LiAlH4 The ether layer is separated washed 2X with water dried over sodium sulfate The ether solution is concentrated the residue vacuum distilled