2-(2,4-dichlorophenoxy)ethanol

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

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

Procedure: The title compound was prepared by the procedures of Example 33 from sulfamoyl chloride and 2-(2,4-dichlorophenoxy)ethanol. The viscous oil obtained solidified and was recrystallized from isopropyl ether to give the solid title compound, mp 75°-77° C., in 35% yield. The viscous oil obtained solidified was recrystallized from isopropyl ether

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

Procedure: To a solution of 2-(2,4-dichlorophenoxy)-1-ethanol (10.0 g) in 1,2-dimethoxyethane (200 mL) was added dropwise a solution of phosphorous tribromide (14 g) in 1,2-dimethoxyethane (20 mL) under ice-cooling. The reaction solution was stirred at room temperature for 20 hours. After the reaction solution was concentrated, the residue was diluted with water and ethyl acetate. When saturated aqueous sodium hydrogencarbonate solution was added to the organic layer, an emulsion was formed, which was filtered through Celite. The filtrate was diluted with diethyl ether and saturated aqueous ammonium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and then concentrated. The residue was purified by silica gel column chromatography to yield the title compound as a pale yellow oil (6.15 g). cooling After the reaction solution was concentrated the residue was diluted with water and ethyl acetate When saturated aqueous sodium hydrogencarbonate solution was added to the organic layer an emulsion was formed which was filtered through Celite The filtrate was diluted with diethyl ether and saturated aqueous ammonium chloride solution The organic layer was dried over anhydrous magnesium sulfate concentrated The residue was purified by silica gel column chromatography

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

Procedure: To a solution of 2,4-dichlorophenoxy acetic acid (15.0 g) in tetrahydrofuran (300 mL) was added dropwise 1.0M borane-tetrahydrofuran complex/tetrahydrofuran solution (96 mL) under ice-cooling over 1.5 hours. The reaction solution was stirred at room temperature for 22 hours. After the reaction solution was concentrated, the residue was diluted with saturated aqueous ammonium chloride solution and ethyl acetate. The organic layer was washed with saturated ammonium chloride, saturated aqueous sodium hydrogencarbonate solution (×2) and saturated ammonium chloride, dried over anhydrous sodium sulfate and then concentrated, to give the title compound as a colorless oil (14 g). cooling over 1.5 hours After the reaction solution was concentrated the residue was diluted with saturated aqueous ammonium chloride solution and ethyl acetate The organic layer was washed with saturated ammonium chloride, saturated aqueous sodium hydrogencarbonate solution (×2) and saturated ammonium chloride dried over anhydrous sodium sulfate concentrated

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

Procedure: To a solution of 2,4-dichlorophenoxy acetic acid (15.0 g) in tetrahydrofuran (300 mL) was added dropwise 1.0M borane-tetrahydrofuran complex/tetrahydrofuran solution (96 mL) under ice-cooling over 1.5 hours. The reaction solution was stirred at room temperature for 22 hours. After the reaction solution was concentrated, the residue was diluted with saturated aqueous ammonium chloride solution and ethyl acetate. The organic layer was washed with saturated ammonium chloride, saturated aqueous sodium hydrogencarbonate solution (×2) and saturated ammonium chloride, dried over anhydrous sodium sulfate and then concentrated, to give the title compound as a colorless oil (14 g). cooling over 1.5 hours After the reaction solution was concentrated the residue was diluted with saturated aqueous ammonium chloride solution and ethyl acetate The organic layer was washed with saturated ammonium chloride, saturated aqueous sodium hydrogencarbonate solution (×2) and saturated ammonium chloride dried over anhydrous sodium sulfate concentrated

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

Procedure: The title compound was prepared by the procedures of Example 33 from sulfamoyl chloride and 2-(2,4-dichlorophenoxy)ethanol. The viscous oil obtained solidified and was recrystallized from isopropyl ether to give the solid title compound, mp 75°-77° C., in 35% yield. The viscous oil obtained solidified was recrystallized from isopropyl ether

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

Procedure: The title compound was prepared by the procedures of Example 33 from sulfamoyl chloride and 2-(2,4-dichlorophenoxy)ethanol. The viscous oil obtained solidified and was recrystallized from isopropyl ether to give the solid title compound, mp 75°-77° C., in 35% yield. The viscous oil obtained solidified was recrystallized from isopropyl ether

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

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

Procedure: To a solution of 10.0 g of 2-(2,4-dichlorophenoxy)-1-ethanol in 1,2-dimethoxyethane (200 ml) was added dropwise a solution of 14 g of phosphorus tribromide in 1,2-dimethoxyethane (20 ml) under ice-cooling. The reaction solution was stirred at room temperature for 20 hours. After the reaction solution was concentrated, the residue was diluted with water and ethyl acetate. Saturated aqueous sodium hydrogencarbonate was added to the organic layer, and the resulting emulsion formed was subjected to Celite filtration. The filtrate was diluted with diethyl ether and saturated aqueous ammonium chloride. The organic layer was dried over anhydrous magnesium sulfate and concentrated. The residue was purified by silica gel column chromatography, to give 6.15 g of the title compound as a pale yellow oil. cooling After the reaction solution was concentrated the residue was diluted with water and ethyl acetate Saturated aqueous sodium hydrogencarbonate was added to the organic layer the resulting emulsion formed was subjected to Celite filtration The filtrate was diluted with diethyl ether and saturated aqueous ammonium chloride The organic layer was dried over anhydrous magnesium sulfate concentrated The residue was purified by silica gel column chromatography

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

Procedure: To a solution of 15.0 g of 2,4-dichlorophenoxyacetic acid in tetrahydrofuran (300 ml) was added dropwise 96 ml of 1.0 M borane-tetrahydrofuran complex/tetrahydrofuran solution under ice-cooling over 1.5 hours. The reaction solution was stirred at room temperature for 22 hours. After the reaction solution was concentrated, the residue was diluted with saturated aqueous ammonium chloride and ethyl acetate. The organic layer was washed with saturated ammonium chloride, saturated aqueous sodium hydrogen carbonate (×2) and saturated ammonium chloride, then dried over anhydrous sodium sulfate and concentrated, to give 14 g the title compound as a colorless oil. cooling over 1.5 hours After the reaction solution was concentrated the residue was diluted with saturated aqueous ammonium chloride and ethyl acetate The organic layer was washed with saturated ammonium chloride, saturated aqueous sodium hydrogen carbonate (×2) and saturated ammonium chloride dried over anhydrous sodium sulfate concentrated

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

Procedure: The title compound was prepared by the procedures of Example 33 from sulfamoyl chloride and 2-(2,4-dichlorophenoxy)ethanol. The viscous oil obtained solidified and was recrystallized from isopropyl ether to give the solid title compound, mp 75°-77° C., in 35% yield. The viscous oil obtained solidified was recrystallized from isopropyl ether

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

Procedure: The title compound was prepared by the procedures of Example 28 from sulfamoyl chloride and 2-(2,4-dichlorophenoxy)ethanol. The viscous oil obtained solidified and was recrystallized from isopropyl ether to give the solid title compound, mp 75°-77° C., in 35% yield. The viscous oil obtained solidified was recrystallized from isopropyl ether