ethyl 8-methylnonanoate

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

Procedure: From the obtained ethyl 8-methylnonanoate, 19.20 g was dissolved in ethanol (72.0 ml) and 2M NaOH aqueous solution (72.0 ml) was slowly added at 0° C. (ice bath). The mixture was heated with stirring using an oil bath at 60° C. for 1 hour, the reaction vessel was returned to room temperature and ethanol was evaporated under reduced pressure. 2M NaOH (30 ml) and water (30 ml) were added to the solution, and the solution was washed with tert-butyl methyl ether (100 ml). The aqueous layer was washed with tert-butyl methyl ether (100 ml) once again. The aqueous layer was carefully acidified with 2M HCl aqueous solution (150 ml), and the mixture was extracted twice with heptane (150 ml). The combined heptane layer was washed with water (100 ml) and then saturated brine (100 ml), dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to give 8-methylnonanoic acid (15.9 g, crude yield 96.6%) as a crude product of a pale-yellow oil. As a result of the GCMS analysis, it contained structurally unidentified impurities A (0.01%), B (0.03%), C (0.04%), and D (0.07%), and the purity of 8-methylnonanoic acid was 99.6%. The mixture was heated at 60° C. for 1 hour was returned to room temperature ethanol was evaporated under reduced pressure 2M NaOH (30 ml) and water (30 ml) were added to the solution the solution was washed with tert-butyl methyl ether (100 ml) The aqueous layer was washed with tert-butyl methyl ether (100 ml) once again the mixture was extracted twice with heptane (150 ml) The combined heptane layer was washed with water (100 ml) saturated brine (100 ml), dried over anhydrous magnesium sulfate filtered concentrated under reduced pressure

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

Procedure: From the obtained ethyl 8-methylnonanoate, 19.20 g was dissolved in ethanol (72.0 ml) and 2M NaOH aqueous solution (72.0 ml) was slowly added at 0° C. (ice bath). The mixture was heated with stirring using an oil bath at 60° C. for 1 hour, the reaction vessel was returned to room temperature and ethanol was evaporated under reduced pressure. 2M NaOH (30 ml) and water (30 ml) were added to the solution, and the solution was washed with tert-butyl methyl ether (100 ml). The aqueous layer was washed with tert-butyl methyl ether (100 ml) once again. The aqueous layer was carefully acidified with 2M HCl aqueous solution (150 ml), and the mixture was extracted twice with heptane (150 ml). The combined heptane layer was washed with water (100 ml) and then saturated brine (100 ml), dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to give 8-methylnonanoic acid (15.9 g, crude yield 96.6%) as a crude product of a pale-yellow oil. As a result of the GCMS analysis, it contained structurally unidentified impurities A (0.01%), B (0.03%), C (0.04%), and D (0.07%), and the purity of 8-methylnonanoic acid was 99.6%. The mixture was heated at 60° C. for 1 hour was returned to room temperature ethanol was evaporated under reduced pressure 2M NaOH (30 ml) and water (30 ml) were added to the solution the solution was washed with tert-butyl methyl ether (100 ml) The aqueous layer was washed with tert-butyl methyl ether (100 ml) once again the mixture was extracted twice with heptane (150 ml) The combined heptane layer was washed with water (100 ml) saturated brine (100 ml), dried over anhydrous magnesium sulfate filtered concentrated under reduced pressure

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

Procedure: LAH (lithium aluminum hydride, 1.10 g, 29.0 mmol) was suspended in ether (50 ml), and the slurry was kept at 0° C. Thereto was slowly added dropwise a solution of 8-methylnonanoic acid ethyl ester (5.81 g, 29.0 mmol) in ether (20 ml). After the completion of the dropwise addition, the slurry was stirred at room temperature for 2 hr and 10% aqueous potassium hydrogen sulfate solution (50 ml) was slowly added to the reaction mixture. Ether (100 ml) was further added, and the aqueous layer was separated from the organic layer. The organic layer was washed with saturated brine (50 ml), and dried over anhydrous magnesium sulfate. Magnesium sulfate was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was distilled under reduced pressure (60 to 65° C./2 mmHg) to give 8-methyl-1-nonanol (4.27 g, 27.0 mmol) as a colorless oil. was kept at 0° C After the completion of the dropwise addition the aqueous layer was separated from the organic layer The organic layer was washed with saturated brine (50 ml) dried over anhydrous magnesium sulfate Magnesium sulfate was filtered off the filtrate was concentrated under reduced pressure The obtained residue was distilled under reduced pressure (60 to 65° C./2 mmHg)

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

Procedure: LAH (lithium aluminum hydride, 1.10 g, 29.0 mmol) was suspended in ether (50 ml), and the slurry was kept at 0° C. Thereto was slowly added dropwise a solution of 8-methylnonanoic acid ethyl ester (5.81 g, 29.0 mmol) in ether (20 ml). After the completion of the dropwise addition, the slurry was stirred at room temperature for 2 hr and 10% aqueous potassium hydrogen sulfate solution (50 ml) was slowly added to the reaction mixture. Ether (100 ml) was further added, and the aqueous layer was separated from the organic layer. The organic layer was washed with saturated brine (50 ml), and dried over anhydrous magnesium sulfate. Magnesium sulfate was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was distilled under reduced pressure (60 to 65° C./2 mmHg) to give 8-methyl-1-nonanol (4.27 g, 27.0 mmol) as a colorless oil. was kept at 0° C After the completion of the dropwise addition the aqueous layer was separated from the organic layer The organic layer was washed with saturated brine (50 ml) dried over anhydrous magnesium sulfate Magnesium sulfate was filtered off the filtrate was concentrated under reduced pressure The obtained residue was distilled under reduced pressure (60 to 65° C./2 mmHg)

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

Procedure: From the obtained ethyl 8-methylnonanoate, 19.20 g was dissolved in ethanol (72.0 ml) and 2M NaOH aqueous solution (72.0 ml) was slowly added at 0° C. (ice bath). The mixture was heated with stirring using an oil bath at 60° C. for 1 hour, the reaction vessel was returned to room temperature and ethanol was evaporated under reduced pressure. 2M NaOH (30 ml) and water (30 ml) were added to the solution, and the solution was washed with tert-butyl methyl ether (100 ml). The aqueous layer was washed with tert-butyl methyl ether (100 ml) once again. The aqueous layer was carefully acidified with 2M HCl aqueous solution (150 ml), and the mixture was extracted twice with heptane (150 ml). The combined heptane layer was washed with water (100 ml) and then saturated brine (100 ml), dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to give 8-methylnonanoic acid (15.9 g, crude yield 96.6%) as a crude product of a pale-yellow oil. As a result of the GCMS analysis, it contained structurally unidentified impurities A (0.01%), B (0.03%), C (0.04%), and D (0.07%), and the purity of 8-methylnonanoic acid was 99.6%. The mixture was heated at 60° C. for 1 hour was returned to room temperature ethanol was evaporated under reduced pressure 2M NaOH (30 ml) and water (30 ml) were added to the solution the solution was washed with tert-butyl methyl ether (100 ml) The aqueous layer was washed with tert-butyl methyl ether (100 ml) once again the mixture was extracted twice with heptane (150 ml) The combined heptane layer was washed with water (100 ml) saturated brine (100 ml), dried over anhydrous magnesium sulfate filtered concentrated under reduced pressure