2-methoxypropan-1-ol

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

Procedure: To dichloromethane (30 mL) mixture of 2-methoxypropan-1-ol (1.6 g, 17.8 mmol) and pyridine (20.0 mL), was added p-toluenesulfonyl chloride (4.07 g, 21.4 mmol) while stirring on ice, and the mixture was stirred at room temperature for five hours. To the mixture, were added water and ethyl acetate. After thoroughly shaking the mixture, the organic layer was separated, and the organic layer was washed with brine and dried over anhydrous magnesium sulfate. The mixture was filtered, and the solvent in the filtrate was then distilled off under reduced pressure. The residue was purified by silica gel column chromatography (a mixed solvent of n-heptane and ethyl acetate: n-heptane/ethyl acetate=2/1) to obtain the title compound (3.12 g, 12.8 mmol). the mixture was stirred at room temperature for five hours After thoroughly shaking the mixture the organic layer was separated the organic layer was washed with brine dried over anhydrous magnesium sulfate The mixture was filtered the solvent in the filtrate was then distilled off under reduced pressure The residue was purified by silica gel column chromatography (a mixed solvent of n-heptane and ethyl acetate

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

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

Procedure: To dichloromethane (30 mL) mixture of 2-methoxypropan-1-ol (1.6 g, 17.8 mmol) and pyridine (20.0 mL), was added p-toluenesulfonyl chloride (4.07 g, 21.4 mmol) while stirring on ice, and the mixture was stirred at room temperature for five hours. To the mixture, were added water and ethyl acetate. After thoroughly shaking the mixture, the organic layer was separated, and the organic layer was washed with brine and dried over anhydrous magnesium sulfate. The mixture was filtered, and the solvent in the filtrate was then distilled off under reduced pressure. The residue was purified by silica gel column chromatography (a mixed solvent of n-heptane and ethyl acetate: n-heptane/ethyl acetate=2/1) to obtain the title compound (3.12 g, 12.8 mmol). the mixture was stirred at room temperature for five hours After thoroughly shaking the mixture the organic layer was separated the organic layer was washed with brine dried over anhydrous magnesium sulfate The mixture was filtered the solvent in the filtrate was then distilled off under reduced pressure The residue was purified by silica gel column chromatography (a mixed solvent of n-heptane and ethyl acetate

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

Procedure: To dichloromethane (30 mL) mixture of 2-methoxypropan-1-ol (1.6 g, 17.8 mmol) and pyridine (20.0 mL), was added p-toluenesulfonyl chloride (4.07 g, 21.4 mmol) while stirring on ice, and the mixture was stirred at room temperature for five hours. To the mixture, were added water and ethyl acetate. After thoroughly shaking the mixture, the organic layer was separated, and the organic layer was washed with brine and dried over anhydrous magnesium sulfate. The mixture was filtered, and the solvent in the filtrate was then distilled off under reduced pressure. The residue was purified by silica gel column chromatography (a mixed solvent of n-heptane and ethyl acetate: n-heptane/ethyl acetate=2/1) to obtain the title compound (3.12 g, 12.8 mmol). the mixture was stirred at room temperature for five hours After thoroughly shaking the mixture the organic layer was separated the organic layer was washed with brine dried over anhydrous magnesium sulfate The mixture was filtered the solvent in the filtrate was then distilled off under reduced pressure The residue was purified by silica gel column chromatography (a mixed solvent of n-heptane and ethyl acetate

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

Conditions: temp:75.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Into a 2 L round-bottom flask was placed hexadecyl bromide (250 g), 2-methoxypropanol (250 mL), and triethylamine (200 mL). The flask was heated without stirring at 75° C. for 96 h and the contents were concentrated on a Rotavap at 75° C. and 20 mbar. To the residue, methyl tert-butyl ether (800 mL) was added. The slurry was vigorously stirred by a mechanical stirrer for 12 h, filtered, washed with 3 portions (400 mL each) of methyl tert-butyl ether, and dried in vacuum to obtain the product as a white solid in nearly quantitative yield. Into a 2 L round-bottom flask was placed The flask was heated the contents were concentrated on a Rotavap at 75° C. To the residue, methyl tert-butyl ether (800 mL) was added The slurry was vigorously stirred by a mechanical stirrer for 12 h filtered washed with 3 portions (400 mL each) of methyl tert-butyl ether dried in vacuum