2-[2-(2-ethoxyethoxy)ethoxy]ethanol

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

Procedure: In a 3-neck, 2 L rbf, NaOH (135 g, 3.37 mol) was added slowly to water (1 L). After the addition was complete, the solution was cooled to room temperature and DCM (2 L) added, followed by triethylene glycol monoethyl ether (500 g, 2.81 mol). p-Toluenesulfonyl chloride (535 g, 2.81 mol) was added portion-wise over a period of 10 minutes, and the mixture refluxed for 2 hours. After cooling to room temperature, the reaction mixture was poured into water (2 L), mixed well and separated. The organic phase was washed with water (2×2 L), dried over MgSO4, filtered and solvent removed by rotary evaporation. The resulting clear, colourless oil was stirred at room temperature with a 10% aqueous NaOH solution (1 L) to hydrolyze unreacted p-toluenesulfonyl chloride. After 18 hours, the material was poured into water (1 L), extracted with chloroform (500 mL) and separated. The organic portion was washed with water (2 L), 10% HCl (2 L) and water (2 L). The material was dried over anhydrous MgSO4, filtered and solvent removed by rotavap to afford (103) as a clear, colourless oil (595 g, 64%). After the addition the mixture refluxed for 2 hours After cooling to room temperature mixed well separated The organic phase was washed with water (2×2 L) dried over MgSO4 filtered solvent removed by rotary evaporation the material was poured into water (1 L) extracted with chloroform (500 mL) separated The organic portion was washed with water (2 L), 10% HCl (2 L) and water (2 L) The material was dried over anhydrous MgSO4 filtered solvent removed by rotavap

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

Procedure: In a 3-neck, 2 L rbf, NaOH (135 g, 3.37 mol) was added slowly to water (1 L). After the addition was complete, the solution was cooled to room temperature and DCM (2 L) added, followed by triethylene glycol monoethyl ether (500 g, 2.81 mol). p-Toluenesulfonyl chloride (535 g, 2.81 mol) was added portion-wise over a period of 10 minutes, and the mixture refluxed for 2 hours. After cooling to room temperature, the reaction mixture was poured into water (2 L), mixed well and separated. The organic phase was washed with water (2×2 L), dried over MgSO4, filtered and solvent removed by rotary evaporation. The resulting clear, colourless oil was stirred at room temperature with a 10% aqueous NaOH solution (1 L) to hydrolyze unreacted p-toluenesulfonyl chloride. After 18 hours, the material was poured into water (1 L), extracted with chloroform (500 mL) and separated. The organic portion was washed with water (2 L), 10% HCl (2 L) and water (2 L). The material was dried over anhydrous MgSO4, filtered and solvent removed by rotavap to afford (103) as a clear, colourless oil (595 g, 64%). After the addition the mixture refluxed for 2 hours After cooling to room temperature mixed well separated The organic phase was washed with water (2×2 L) dried over MgSO4 filtered solvent removed by rotary evaporation the material was poured into water (1 L) extracted with chloroform (500 mL) separated The organic portion was washed with water (2 L), 10% HCl (2 L) and water (2 L) The material was dried over anhydrous MgSO4 filtered solvent removed by rotavap

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

Procedure: A mixture of 400 g triethylene glycol monoethyl ether (2.2 mol), 48 g paraformaldehyde (1.6 mol), 150 ml toluene and 10 g of an acid ion exchange resin was refluxed for 6 hours in a 1 liter flask equipped with a water separator and reflux condenser. Filtration of the product followed by distillation gave a quantitative yield of the desired product. was refluxed for 6 hours in a 1 liter flask reflux condenser Filtration of the product followed by distillation

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

Procedure: A mixture of 400 g triethylene glycol monoethyl ether (2.2 mol), 48 g paraformaldehyde (1.6 mol), 150 ml toluene and 10 g of an acid ion exchange resin was refluxed for 6 hours in a 1 liter flask equipped with a water separator and reflux condenser. Filtration of the product followed by distillation gave a quantitative yield of the desired product. was refluxed for 6 hours in a 1 liter flask reflux condenser Filtration of the product followed by distillation

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

Procedure: p-Toluenesulfonyl chloride (12.583 g, 66.0 mmol) was added to an ice-cooled solution of triethylene glycol monoethyl ether (10.484 ml, 10.694 g, 60.0 mmol) in pyridine (9.7 ml). After being stirred for 3.5 h the reaction was diluted with 10% hydrochloric acid and extracted with ethyl acetate. The organic phase was separated, washed with 10% hydrochloric acid, dried over MgSO4 and concentrated in vacuo to afford sufficiently pure p-toluenesulfonate of triethylene glycol monoethyl ether (19.92 g, 59.9 mmol, 100%) as a reddish liquid. The obtained tosylate (19.5 g, 58.7 mmol) was dissolved in 33% solution of methylamine in methanol (24 ml) and refluxed for 18 h, cooled and concentrated in vacuo. The residue was dissolved in 5% HCl and washed 3 times with dichloromethane. The combined organic solution was back extracted with 5% HCl. All aqueous extracts were combined and mixed with a solution of sodium hydroxide (6 g) in water (14 ml). The resultant solution was extracted with dichloromethane. The combined organic solution was washed with water, dried over MgSO4 and concentrated in vacuo to afford crude 2-(2-(2-ethoxyethoxy)ethoxy)-N-methylethanamine (6.50 g) as a yellowish liquid, which was then used further without additional purification. The crude 2-(2-(2-ethoxyethoxy)ethoxy)-N-methylethanamine (0.426 g, 1.86 mmol) was added to suspension of compound 1 (1.07 g, 0.928 mmol) in a mixture of triethylamine (1.293 ml, 0.939 g, 9.28 mmol) and DMF (5 ml). The reaction mixture was stirred overnight and diluted with ether. The obtained solid was collected by filtration, washed with ether, and dried in vacuo to afford the desired compound 2c (0.93 g, 0.80 mmol, 86%) as a pale solid. The crude material was used in the next step without further purification. extracted with ethyl acetate The organic phase was separated washed with 10% hydrochloric acid dried over MgSO4 concentrated in vacuo

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

Procedure: 14.8 g (0.083 mole) of triethylene glycol monoethyl ether was added dropwise to a mixture consisting of 1.6 g (0.042 mole) of sodium borohydride, 10 ml of xylene and 5 g (0.027 mole) of methyl caprate at 95° C. over two hours while agitating the mixture. Subsequently, the mixture was agitated at the same temperature for 1.5 hours. After cooling to room temperature, the mixture was neutralized with dilute sulfuric acid. As a result, n-decanol was obtained in 99% yield. Subsequently, the mixture was agitated at the same temperature for 1.5 hours

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

Procedure: In 20 ml pyridine was dissolved 2.0 g (0.0167 mol) of triethylene glycol monoethyl ether, and while stirring at room temperature, 1.8 g (0.0049 mol) of 2-chloro-5-(2-chloro-4-trifluoromethylphenoxy)benzoyl chloride was added. After 4-hour stirring, the reaction fluid was poured into 200 ml of water, and extracted with benzene. The extract was washed with a dilute aqueous solution of caustic soda and then with dilute hydrochloric acid. By concentration 1.4 g (0.0031 mol) of the intended product was obtained as a viscous oily substance, yield 63.3%, nD28 1.5175. After 4-hour stirring extracted with benzene The extract was washed with a dilute aqueous solution of caustic soda

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

Procedure: In a 3-neck, 2 L rbf, NaOH (135 g, 3.37 mol) was added slowly to water (1 L). After the addition was complete, the solution was cooled to room temperature and DCM (2 L) added, followed by triethylene glycol monoethyl ether (500 g, 2.81 mol). p-Toluenesulfonyl chloride (535 g, 2.81 mol) was added portion-wise over a period of 10 minutes, and the mixture refluxed for 2 hours. After cooling to room temperature, the reaction mixture was poured into water (2 L), mixed well and separated. The organic phase was washed with water (2×2 L), dried over MgSO4, filtered and solvent removed by rotary evaporation. The resulting clear, colourless oil was stirred at room temperature with a 10% aqueous NaOH solution (1 L) to hydrolyze unreacted p-toluenesulfonyl chloride. After 18 hours, the material was poured into water (1 L), extracted with chloroform (500 mL) and separated. The organic portion was washed with water (2 L), 10% HCl (2 L) and water (2 L). The material was dried over anhydrous MgSO4, filtered and solvent removed by rotavap to afford (103) as a clear, colourless oil (595 g, 64%). After the addition the mixture refluxed for 2 hours After cooling to room temperature mixed well separated The organic phase was washed with water (2×2 L) dried over MgSO4 filtered solvent removed by rotary evaporation the material was poured into water (1 L) extracted with chloroform (500 mL) separated The organic portion was washed with water (2 L), 10% HCl (2 L) and water (2 L) The material was dried over anhydrous MgSO4 filtered solvent removed by rotavap