2-octyloxirane

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

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: Using the method of Example 5, supra, 1,2-epoxydecane (204 mg, 1.0 mmol) and 1,1-dimethyl-2-(4-methoxyphenyl)ethylamine (197 mg, 1.1 mmol) were used to prepare 73 mg of the title compound as a clear, colorless oil: GC/EI-MS, m/z (rel. int.) 214 (M-121, 100), 196 (27.8), 163 (10), 121 (2.2); 1H-NMR (CDCl3) δ 7.08 (2H, d, J=8.6), 6.83 (2H, d, J=8.6), 3.79 (3H, s), 3.53 (1H, m), 2.79 (1H, dd, J=11.7 and 2.9), 2.67 (2H, s), 2.42 (1H, dd, J=12.6 and 9.6), 1.26 (18 H, m), 1.08 (3H, s), 0.88 (3H, t, J=6.6); 13C-NMR (CDCl3) δ 158.2, 131.4, 129.8, 113.5, 77.2, 69.8, 55.2, 53.8, 47.8, 46.5, 35.1, 31.9, 29.8, 29.7, 29.6, 29.3, 26.6, 26.4, 25.7, 22.7, 14.1; FT-IR (film) cm-1 3399 (broad s), 1612, 1512, 1246, 1039, 823.

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: As described in Example 1, 1 mol of 1,2-epoxydecane was caused to react with 5 times the molar quantity of n-butanol and 0.04 gm-atom of sodium. After distillation of the excess alcohol, the reaction with 10 mols of ethylene oxide was conducted in an autoclave under the conditions described in Example 1, except for the addition of the sodium methylate catalyst. The product thus obtained had a cloud point of 64°C. After distillation of the excess alcohol The product thus obtained

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

Procedure: As described in Example 1, 1 mol of 1,2-epoxydecane was caused to react with 5 times the molar quantity of n-butanol and 0.04 gm-atom of sodium. After distillation of the excess alcohol, the reaction with 10 mols of ethylene oxide was conducted in an autoclave under the conditions described in Example 1, except for the addition of the sodium methylate catalyst. The product thus obtained had a cloud point of 64°C. After distillation of the excess alcohol The product thus obtained

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 0.46 gm (0.02 gm-atom) of sodium were added to 185 gm (2.5 mols) of n-butanol. After dissolution of the sodium, the temperature was raised to 100°C, and an amount of 78.2 gm (0.5 mol) of 1,2-epoxy decane was added in drops within 30 minutes while stirring. The reaction mixture was maintained at 100°C for 4 hours. Then the excess alcohol was distilled, and by subsequent vacuum distillation at 100° to 120°C and 0.06 Torr . the 2-hydroxy-decyl-n-butyl ether was separated from the higher boiling by-product. In this manner the intermediate product 2-hydroxydecyl-n-butyl ether (refractive index nD20 = 1.4392) was obtained in a yield of 87%. The reaction mixture was maintained at 100°C for 4 hours Then the excess alcohol was distilled by subsequent vacuum distillation at 100° to 120°C the 2-hydroxy-decyl-n-butyl ether was separated from the higher boiling by-product

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 0.46 gm (0.02 gm-atom) of sodium were added to 185 gm (2.5 mols) of n-butanol. After dissolution of the sodium, the temperature was raised to 100°C, and an amount of 78.2 gm (0.5 mol) of 1,2-epoxy decane was added in drops within 30 minutes while stirring. The reaction mixture was maintained at 100°C for 4 hours. Then the excess alcohol was distilled, and by subsequent vacuum distillation at 100° to 120°C and 0.06 Torr . the 2-hydroxy-decyl-n-butyl ether was separated from the higher boiling by-product. In this manner the intermediate product 2-hydroxydecyl-n-butyl ether (refractive index nD20 = 1.4392) was obtained in a yield of 87%. The reaction mixture was maintained at 100°C for 4 hours Then the excess alcohol was distilled by subsequent vacuum distillation at 100° to 120°C the 2-hydroxy-decyl-n-butyl ether was separated from the higher boiling by-product

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

Procedure: A homogeneous clear solution is prepared by adding 3 moles of acetone to a (1:1:1) mixture of 1-nonene oxide, 1-decene oxide, and 1-undecene oxide at room temperature. After adding 50 grams of 5% aqueous sulfuric acid to the solution, the acetone is evaporated off and the resulting solution is neutralized by adding an aqueous sodium hydroxide. The neutralized solution is extracted with pet ether and the extract dried over anhydrous magnesium sulfate. The pet ether is stripped off and a mixture of 1,2-nonanediol, 1,2-decanediol and 1,2 undecanediol is obtained by distilling under vacuo. A homogeneous clear solution is prepared the acetone is evaporated off by adding an aqueous sodium hydroxide The neutralized solution is extracted with pet ether the extract dried over anhydrous magnesium sulfate a mixture of 1,2-nonanediol, 1,2-decanediol

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

Procedure: A homogeneous clear solution is prepared by adding 3 moles of acetone to 1 mole of a mixture of 1-nonene oxide and 1-decene oxide at room temperature. After 50 grams of 5% aqueous sulfuric acid to the solution, the acetone is evaporated off and the resulting solution is neutralized by adding an aqueous sodium hydroxide. The neutralized solution is extracted with pet ether and the extract dried over anhydrous magnesium sulfate. The pet ether is stripped off and a mixture of 1,2-nonanediol and 1,2-decanediol is obtained by distilling under vacuo. A homogeneous clear solution is prepared After 50 grams of 5% aqueous sulfuric acid to the solution, the acetone is evaporated off by adding an aqueous sodium hydroxide The neutralized solution is extracted with pet ether the extract dried over anhydrous magnesium sulfate a mixture of 1,2-nonanediol