dodec-9-yn-1-ol

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: The same procedure for 8-nonyn-1-ol was followed with 9-dodecyn-1-ol (4.68 g, 25.7 mmol), KH(3.09 g, 77.0 mmol), and 1,3-diaminopropane (70 mL). This produced 4.33 g of yellow oil (93%): IR (neat) ν 3317,2930, 2121 cm−1; 1H—NMR δ 3.62 (t, 2H, J=6.6 Hz), 2.17 (td, 2H, J=2.6 Hz, 7.1 Hz), 1.93 (t, 1H, J=2.6 Hz), 1.76 (bs, 1H), 1.55 (m, 4H), 1.28 bm, 12H); 13C—NMR δ 84.8, 68.0, 63.0, 32.7, 29.5, 29.4 (2C), 29.0, 28.7, 28.4, 25.7, 18.4; MS m/z 189.18 (M++Li).

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

Procedure: 6212 g (34.8 moles) of dodec-9-yn-1-ol and 316 g of N-methylmorpholine are dissolved in 46 l of methanol in a 100 l glass flask, and 62 g of a catalyst (0.7% Pd and 3.1% of Zn on a CaCO3 carrier) are suspended in the solution. Thereafter, the stirred suspension is flushed with nitrogen, and hydrogenation is carried out at from 0° to 5° C. and under a hydrogen pressure of 0.1 bar above atmospheric pressure until the absorption of hydrogen is complete. The methanol and morpholine are stripped off to give 6,200 g of dodec-9-en-1-ol containing 96.6% of the cis compound and 2.1% of the trans compound. Thereafter, the stirred suspension is flushed with nitrogen, and hydrogenation is carried out at from 0° to 5° C. and under a hydrogen until the absorption of hydrogen

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

Procedure: 6212 g (34.8 moles) of dodec-9-yn-1-ol and 316 g of N-methylmorpholine are dissolved in 46 l of methanol in a 100 l glass flask, and 62 g of a catalyst (0.7% Pd and 3.1% of Zn on a CaCO3 carrier) are suspended in the solution. Thereafter, the stirred suspension is flushed with nitrogen, and hydrogenation is carried out at from 0° to 5° C. and under a hydrogen pressure of 0.1 bar above atmospheric pressure until the absorption of hydrogen is complete. The methanol and morpholine are stripped off to give 6,200 g of dodec-9-en-1-ol containing 96.6% of the cis compound and 2.1% of the trans compound. Thereafter, the stirred suspension is flushed with nitrogen, and hydrogenation is carried out at from 0° to 5° C. and under a hydrogen until the absorption of hydrogen

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

Procedure: The same procedure for 8-nonyn-1-ol was followed with 9-dodecyn-1-ol (4.68 g, 25.7 mmol), KH(3.09 g, 77.0 mmol), and 1,3-diaminopropane (70 mL). This produced 4.33 g of yellow oil (93%): IR (neat) ν 3317,2930, 2121 cm−1; 1H—NMR δ 3.62 (t, 2H, J=6.6 Hz), 2.17 (td, 2H, J=2.6 Hz, 7.1 Hz), 1.93 (t, 1H, J=2.6 Hz), 1.76 (bs, 1H), 1.55 (m, 4H), 1.28 bm, 12H); 13C—NMR δ 84.8, 68.0, 63.0, 32.7, 29.5, 29.4 (2C), 29.0, 28.7, 28.4, 25.7, 18.4; MS m/z 189.18 (M++Li).

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

Procedure: The same procedure for 8-nonyn-1-ol was followed with 9-dodecyn-1-ol (4.68 g, 25.7 mmol), KH(3.09 g, 77.0 mmol), and 1,3-diaminopropane (70 mL). This produced 4.33 g of yellow oil (93%): IR (neat) ν 3317,2930, 2121 cm−1; 1H—NMR δ 3.62 (t, 2H, J=6.6 Hz), 2.17 (td, 2H, J=2.6 Hz, 7.1 Hz), 1.93 (t, 1H, J=2.6 Hz), 1.76 (bs, 1H), 1.55 (m, 4H), 1.28 bm, 12H); 13C—NMR δ 84.8, 68.0, 63.0, 32.7, 29.5, 29.4 (2C), 29.0, 28.7, 28.4, 25.7, 18.4; MS m/z 189.18 (M++Li).

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: Triethylamine (4.3 ml) was added to a solution of 9-dodecyn-1-ol (5.1 g, 28 mmol) in 50 ml CH2Cl2, and the mixture was then added dropwise at 0° C. to a solution of methanesulfonyl chloride (2,2 ml, 28 mmol) in 10 ml CH2Cl2. The mixture was stirred another 4 hours at room temperature, then cooled to 0°-5° C. The solution was washed with cold 5% aqueous sodium bicarbonate, cold 1N HCl, cold water, then saturated brine. The extract was dried over Na2SO4 and filtered and evaporated. The solvent was evaporated to leave crude 1-(9-dodecynyl) methanesulfonate. cooled to 0°-5° C The solution was washed with cold 5% aqueous sodium bicarbonate, cold 1N HCl, cold water The extract was dried over Na2SO4 filtered evaporated The solvent was evaporated

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

Procedure: 6212 g (34.8 moles) of dodec-9-yn-1-ol and 316 g of N-methylmorpholine are dissolved in 46 l of methanol in a 100 l glass flask, and 62 g of a catalyst (0.7% Pd and 3.1% of Zn on a CaCO3 carrier) are suspended in the solution. Thereafter, the stirred suspension is flushed with nitrogen, and hydrogenation is carried out at from 0° to 5° C. and under a hydrogen pressure of 0.1 bar above atmospheric pressure until the absorption of hydrogen is complete. The methanol and morpholine are stripped off to give 6,200 g of dodec-9-en-1-ol containing 96.6% of the cis compound and 2.1% of the trans compound. Thereafter, the stirred suspension is flushed with nitrogen, and hydrogenation is carried out at from 0° to 5° C. and under a hydrogen until the absorption of hydrogen

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

Procedure: The same procedure for 8-nonyn-1-ol was followed with 9-dodecyn-1-ol (4.68 g, 25.7 mmol), KH(3.09 g, 77.0 mmol), and 1,3-diaminopropane (70 mL). This produced 4.33 g of yellow oil (93%): IR (neat) ν 3317,2930, 2121 cm−1; 1H—NMR δ 3.62 (t, 2H, J=6.6 Hz), 2.17 (td, 2H, J=2.6 Hz, 7.1 Hz), 1.93 (t, 1H, J=2.6 Hz), 1.76 (bs, 1H), 1.55 (m, 4H), 1.28 bm, 12H); 13C—NMR δ 84.8, 68.0, 63.0, 32.7, 29.5, 29.4 (2C), 29.0, 28.7, 28.4, 25.7, 18.4; MS m/z 189.18 (M++Li).