2-(2-methoxyethoxy)phenol

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

Procedure: 4.5 g of 1-chloro-3-(2,6-dimethylpiperidino)-2-propanol is added to a mixture of 3.4 g of 2-(2-methoxyethoxy)phenol, 2.8 g of anhydrous potassium carbonate and 70 ml of acetone, and the resulting mixture is refluxed with stirring for 20 hours. The insoluble matter is then filtered off, and the filtrate is concentrated under reduced pressure. To the residue is added ether, and the ethereal solution is extracted with two 80 ml portions of 10% hydrochloric acid. The aqueous layer is made alkaline with sodium hyroxide, and the separated oil is extracted twice with ether. The ether layer is dried over anhydrous potassium carbonate, and the ether is removed to give 4.6 g of 1-(2,6-dimethylpiperidino)-3-[2-(2-methoxyethoxy)phenoxy]-2-propanol, melting at 92°-94°C. the resulting mixture is refluxed The insoluble matter is then filtered off the filtrate is concentrated under reduced pressure To the residue is added ether the ethereal solution is extracted with two 80 ml portions of 10% hydrochloric acid the separated oil is extracted twice with ether The ether layer is dried over anhydrous potassium carbonate the ether is removed

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

Procedure: 4.5 g of 1-chloro-3-(2,6-dimethylpiperidino)-2-propanol is added to a mixture of 3.4 g of 2-(2-methoxyethoxy)phenol, 2.8 g of anhydrous potassium carbonate and 70 ml of acetone, and the resulting mixture is refluxed with stirring for 20 hours. The insoluble matter is then filtered off, and the filtrate is concentrated under reduced pressure. To the residue is added ether, and the ethereal solution is extracted with two 80 ml portions of 10% hydrochloric acid. The aqueous layer is made alkaline with sodium hyroxide, and the separated oil is extracted twice with ether. The ether layer is dried over anhydrous potassium carbonate, and the ether is removed to give 4.6 g of 1-(2,6-dimethylpiperidino)-3-[2-(2-methoxyethoxy)phenoxy]-2-propanol, melting at 92°-94°C. the resulting mixture is refluxed The insoluble matter is then filtered off the filtrate is concentrated under reduced pressure To the residue is added ether the ethereal solution is extracted with two 80 ml portions of 10% hydrochloric acid the separated oil is extracted twice with ether The ether layer is dried over anhydrous potassium carbonate the ether is removed

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

Procedure: Catechol (10.0 g, 91 mmol), bromoethylmethylether (12.6 g, 91 mmol), and potassium carbonate (12.6 g, 91 mmol) were mixed in ethanol (100 ml) and refluxed for 15 h. The solvent was evaporated and dichioromethane (200 ml) was added. The inorganics were filtered off and the solvent was removed in vacuum. Chromatography on silica gel with 0.5% methanol in dichloromethane as the eluent gave the title compound. Yield 4.5 g, 29%. refluxed for 15 h The solvent was evaporated dichioromethane (200 ml) was added The inorganics were filtered off the solvent was removed in vacuum

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

Procedure: Catechol (10.0 g, 91 mmol), bromoethylmethylether (12.6 g, 91 mmol), and potassium carbonate (12.6 g, 91 mmol) were mixed in ethanol (100 ml) and refluxed for 15 h. The solvent was evaporated and dichloromethane (200 ml) was added. The inorganics were filtered off and the solvent was removed in vacuum. Chromatography on silica gel with 0.5% methanol in dichloromethane as the eluent gave the title compound. Yield 4.5 g, 29%. refluxed for 15 h The solvent was evaporated dichloromethane (200 ml) was added The inorganics were filtered off the solvent was removed in vacuum

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

Procedure: 4.5 g of 1-chloro-3-(2,6-dimethylpiperidino)-2-propanol is added to a mixture of 3.4 g of 2-(2-methoxyethoxy)phenol, 2.8 g of anhydrous potassium carbonate and 70 ml of acetone, and the resulting mixture is refluxed with stirring for 20 hours. The insoluble matter is then filtered off, and the filtrate is concentrated under reduced pressure. To the residue is added ether, and the ethereal solution is extracted with two 80 ml portions of 10% hydrochloric acid. The aqueous layer is made alkaline with sodium hyroxide, and the separated oil is extracted twice with ether. The ether layer is dried over anhydrous potassium carbonate, and the ether is removed to give 4.6 g of 1-(2,6-dimethylpiperidino)-3-[2-(2-methoxyethoxy)phenoxy]-2-propanol, melting at 92°-94°C. the resulting mixture is refluxed The insoluble matter is then filtered off the filtrate is concentrated under reduced pressure To the residue is added ether the ethereal solution is extracted with two 80 ml portions of 10% hydrochloric acid the separated oil is extracted twice with ether The ether layer is dried over anhydrous potassium carbonate the ether is removed

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

Procedure: Catechol (10.0 g, 91 mmol), bromoethylmethylether (12.6 g, 91 mmol), and potassium carbonate (12.6 g, 91 mmol) were mixed in ethanol (100 ml) and refluxed for 15 h. The solvent was evaporated and dichioromethane (200 ml) was added. The inorganics were filtered off and the solvent was removed in vacuum. Chromatography on silica gel with 0.5% methanol in dichloromethane as the eluent gave the title compound. Yield 4.5 g, 29%. refluxed for 15 h The solvent was evaporated dichioromethane (200 ml) was added The inorganics were filtered off the solvent was removed in vacuum