9-acetyloxynonanoic acid

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

Procedure: 9-Decenyl acetate (100 mg) was dissolved in DMF (10 mL), and OsO4 (0.06 mL, 2.5% in tBuOH) was added and stirred for 5 min. OXONE (1.23 g) was added in one portion and the reaction had a final volume (12 mL). The reaction was stirred at room temperature for 3 hours or until the solution becomes colorless. This usually marks the completion of the reaction which was verified by TLC or GC. Na2SO3 (600 mg) was added, to reduce the remaining Os(VIII), and stirred for an additional hour or until solution became dark brown/black. EtOAc was added to extract the products and 1N HCl was used to dissolve the salts. The organic extract was washed with 1N HCl (50 mL×3) and brine (50 mL), dried over Na2SO4, and the solvent was removed under reduced pressure to obtain the crude product. 9-Acetoxy nonanoic acid was obtained in 93% yield without the need for further purification. The reaction was stirred at room temperature for 3 hours or until the solution the completion of the reaction which stirred for an additional hour or until solution to extract the products and 1N HCl to dissolve the salts The organic extract was washed with 1N HCl (50 mL×3) and brine (50 mL) dried over Na2SO4 the solvent was removed under reduced pressure to obtain the crude product

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

Procedure: 9-Decenyl acetate (100 mg) was dissolved in DMF (10 mL), and OsO4 (0.06 mL, 2.5% in tBuOH) was added and stirred for 5 min. OXONE (1.23 g) was added in one portion and the reaction had a final volume (12 mL). The reaction was stirred at room temperature for 3 hours or until the solution becomes colorless. This usually marks the completion of the reaction which was verified by TLC or GC. Na2SO3 (600 mg) was added, to reduce the remaining Os(VIII), and stirred for an additional hour or until solution became dark brown/black. EtOAc was added to extract the products and 1N HCl was used to dissolve the salts. The organic extract was washed with 1N HCl (50 mL×3) and brine (50 mL), dried over Na2SO4, and the solvent was removed under reduced pressure to obtain the crude product. 9-Acetoxy nonanoic acid was obtained in 93% yield without the need for further purification. The reaction was stirred at room temperature for 3 hours or until the solution the completion of the reaction which stirred for an additional hour or until solution to extract the products and 1N HCl to dissolve the salts The organic extract was washed with 1N HCl (50 mL×3) and brine (50 mL) dried over Na2SO4 the solvent was removed under reduced pressure to obtain the crude product

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

Procedure: 9-Hydroxynonanoic acid (8.7 g, 50 mmol) in pyridine (8.1 ml, 100 mmol) was treated with acetic anhydride (4.7 ml, 50 mmol) at below 20° C. for 2 h. The mixture was poured onto ice and acidified. Two ether extractions gave 9-acetoxynonanoic acid as a colourless oil (10.8 g, 100%); δH (CDCl3) 10.0(1H, s, CO2H), 4.0(2H, t, H9), 2.3(2H, m, H2), 2.0(3H, s, OAC), 1.1-1.8(12H, m, H3-H8). The mixture was poured onto ice Two ether extractions

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

Procedure: 9-Hydroxynonanoic acid (8.7 g, 50 mmol) in pyridine (8.1 ml, 100 mmol) was treated with acetic anhydride (4.7 ml, 50 mmol) at below 20° C. for 2 h. The mixture was poured onto ice and acidified. Two ether extractions gave 9-acetoxynonanoic acid as a colourless oil (10.8 g, 100%); δH (CDCl3) 10.0(1H, s, CO2H), 4.0(2H, t, H9), 2.3(2H, m, H2), 2.0(3H, s, OAC), 1.1-1.8(12H, m, H3-H8). The mixture was poured onto ice Two ether extractions

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

Procedure: 9-Hydroxynonanoic acid (8.7 g, 50 mmol) in pyridine (8.1 ml, 100 mmol) was treated with acetic anhydride (4.7 ml, 50 mmol) at below 20° C. for 2 h. The mixture was poured onto ice and acidified. Two ether extractions gave 9-acetoxynonanoic acid as a colourless oil (10.8 g, 100%); δH (CDCl3) 10.0(1H, s, CO2H), 4.0(2H, t, H9), 2.3(2H, m, H2), 2.0(3H, s, OAC), 1.1-1.8(12H, m, H3-H8). The mixture was poured onto ice Two ether extractions

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

Procedure: 9-Hydroxynonanoic acid (8.7 g, 50 mmol) in pyridine (8.1 ml, 100 mmol) was treated with acetic anhydride (4.7 ml, 50 mmol) at below 20° C. for 2 h. The mixture was poured onto ice and acidified. Two ether extractions gave 9-acetoxynonanoic acid as a colourless oil (10.8 g, 100%); δH (CDCl3) 10.0 (1H, s, CO2H), 4.0 (2H, t, H9), 2.3 (2H, m, H2), 2.0 (3H, s, OAC), 1.1-1.8 (12H, m, H3-H8). The mixture was poured onto ice Two ether extractions