decane-1,2-diol

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

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

Conditions: temp:55.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Powdered decane-1,2-diol (0.25 moles) is stirred at room temperature and very well powdered sodium hydroxide (0.25 moles) is added in portions. Gentle heating of the mixture to 55° C. gives a viscous yellow paste. Sodium chloroacetate (0.25 moles) is now added in portions over 10 minutes. The white mobile paste produced is stirred at 70°-60° C. for 1.75 h. After cooling to 20° C., 100 ml of petroleum ether is added followed by water. After separation of phases (aided by acetone) the aqueous phase is run off and acidified to pH 1.5 using 98% sulphuric acid. The oil produced is taken up into 2×375 ml diethyl ether which is then dried and evaporated to leave the title product as a clear oil (63%). gives a viscous yellow paste The white mobile paste produced After cooling to 20° C. After separation of phases (aided by acetone) the aqueous phase The oil produced is then dried evaporated

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a well-stirred solution of bis-1,4-(9'-O-dihydroquinidine)phthalazine (7.8 mg, 0.01 mmol), potassium ferricyanide (0.99 g, 3 mmol), potassium carbonate (0.42 g, 3 mmol), and osmium tetroxide (0.1 mL of a 0.1M toluene solution, 0.01 mmol) in 15 mL of a tert-butyl alcohol-water (1:1, v/v) at 0° C., 1-decene (0.14 g, 0.19 mL, 1 mmol) was added in one portion. The mixture was stirred for 24 h at 0° C. Solid sodium sulfite (1.5 g) was added and the mixture was stirred for an additional hour, and then warmed up to room temperature. Ethyl acetate (10 mL) was added to the reaction mixture, and aqueous layer was extracted with ethyl acetate (3×5 mL). Combined organic layer was dried over anhydrous magnesium sulfate, and concentrated in vacuo. Crude product was purified by flash chromatography (silica gel, hexanes/EtOAc) to afford decane 1,2-diol as a white solid (0.145 g, 83%). HPLC analysis of the bis-Mosher ester of this crude decane 1,2 diol gave 84% ee. the mixture was stirred for an additional hour warmed up to room temperature was extracted with ethyl acetate (3×5 mL) Combined organic layer was dried over anhydrous magnesium sulfate concentrated in vacuo Crude product was purified by flash chromatography (silica gel, hexanes/EtOAc)

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a well-stirred solution of bis-1,4-(9'-O-dihydroquinidine)phthalazine (7.8 mg, 0.01 mmol), potassium ferricyanide (0.99 g, 3 mmol), potassium carbonate (0.42 g, 3 mmol), and osmium tetroxide (0.1 mL of a 0.1M toluene solution, 0.01 mmol) in 15 mL of a tert-butyl alcohol-water (1:1, v/v) at 0° C., 1-decene (0.14 g, 0.19 mL, 1 mmol) was added in one portion. The mixture was stirred for 24 h at 0° C. Solid sodium sulfite (1.5 g) was added and the mixture was stirred for an additional hour, and then warmed up to room temperature. Ethyl acetate (10 mL) was added to the reaction mixture, and aqueous layer was extracted with ethyl acetate (3×5 mL). Combined organic layer was dried over anhydrous magnesium sulfate, and concentrated in vacuo. Crude product was purified by flash chromatography (silica gel, hexanes/EtOAc) to afford decane 1,2-diol as a white solid (0.145 g, 83%). HPLC analysis of the bis-Mosher ester of this crude decane 1,2 diol gave 84% ee. the mixture was stirred for an additional hour warmed up to room temperature was extracted with ethyl acetate (3×5 mL) Combined organic layer was dried over anhydrous magnesium sulfate concentrated in vacuo Crude product was purified by flash chromatography (silica gel, hexanes/EtOAc)

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

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

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 1-decene 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 1,2-decanediol 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

Conditions: temp:55.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Powdered decane-1,2-diol (0.25 moles) is stirred at room temperature and very well powdered sodium hydroxide (0.25 moles) is added in portions. Gentle heating of the mixture to 55° C. gives a viscous yellow paste. Sodium chloroacetate (0.25 moles) is now added in portions over 10 minutes. The white mobile paste produced is stirred at 70°-60° C. for 1.75 h. After cooling to 20° C., 100 ml of petroleum ether is added followed by water. After separation of phases (aided by acetone) the aqueous phase is run off and acidified to pH 1.5 using 98% sulphuric acid. The oil produced is taken up into 2×375 ml diethyl ether which is then dried and evaporated to leave the title product as a clear oil (63%). gives a viscous yellow paste The white mobile paste produced After cooling to 20° C. After separation of phases (aided by acetone) the aqueous phase The oil produced is then dried evaporated

Conditions: temp:55.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Powdered decane-1,2-diol (0.25 moles) is stirred at room temperature and very well powdered sodium hydroxide (0.25 moles) is added in portions. Gentle heating of the mixture to 55° C. gives a viscous yellow paste. Sodium chloroacetate (0.25 moles) is now added in portions over 10 minutes. The white mobile paste produced is stirred at 70°-60° C. for 1.75 h. After cooling to 20° C., 100 ml of petroleum ether is added followed by water. After separation of phases (aided by acetone) the aqueous phase is run off and acidified to pH 1.5 using 98% sulphuric acid. The oil produced is taken up into 2×375 ml diethyl ether which is then dried and evaporated to leave the title product as a clear oil (63%). gives a viscous yellow paste The white mobile paste produced After cooling to 20° C. After separation of phases (aided by acetone) the aqueous phase The oil produced is then dried evaporated

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a well-stirred solution of bis-1,4-(9'-O-dihydroquinidine)phthalazine (7.8 mg, 0.01 mmol), potassium ferricyanide (0.99 g, 3 mmol), potassium carbonate (0.42 g, 3 mmol), and osmium tetroxide (0.1 mL of a 0.1M toluene solution, 0.01 mmol) in 15 mL of a tert-butyl alcohol-water (1:1, v/v) at 0° C., 1-decene (0.14 g, 0.19 mL, 1 mmol) was added in one portion. The mixture was stirred for 24 h at 0° C. Solid sodium sulfite (1.5 g) was added and the mixture was stirred for an additional hour, and then warmed up to room temperature. Ethyl acetate (10 mL) was added to the reaction mixture, and aqueous layer was extracted with ethyl acetate (3×5 mL). Combined organic layer was dried over anhydrous magnesium sulfate, and concentrated in vacuo. Crude product was purified by flash chromatography (silica gel, hexanes/EtOAc) to afford decane 1,2-diol as a white solid (0.145 g, 83%). HPLC analysis of the bis-Mosher ester of this crude decane 1,2 diol gave 84% ee. the mixture was stirred for an additional hour warmed up to room temperature was extracted with ethyl acetate (3×5 mL) Combined organic layer was dried over anhydrous magnesium sulfate concentrated in vacuo Crude product was purified by flash chromatography (silica gel, hexanes/EtOAc)

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