1-methoxy-2-phenoxybenzene

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

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

Procedure: A mixture of 10 g of o-phenoxyanisol, 80 ml of hydroiodic acid (52%), 80 ml of acetic acid and 40 ml of acetic anhydride was refluxed for 1.5 hours. After being cooled, the reaction mixture was poured into ice-water to deposit a precipitate. The precipitate was dissolved in ether, and the solution was washed with an aqueous saturated sodium chloride solution, an aqueous saturated thiosulfuric acid aqueous solution and then an aqueous saturated sodium chloride solution. This ether solution was dried over anhydrous sodium sulfate, and the solvent was removed to give yellow solids. The solids were dissolved in acetic acid and stirred. The mixture was poured into cold water to deposit crystals. The crystals were washed with water and then with n-hexane, and dried at 80° C. under reduced pressure to obtain 7.8 g of o-phenoxyphenol as slightly yellow powders. was refluxed for 1.5 hours After being cooled the solution was washed with an aqueous saturated sodium chloride solution This ether solution was dried over anhydrous sodium sulfate the solvent was removed to give yellow solids The crystals were washed with water with n-hexane, and dried at 80° C. under reduced pressure

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

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

Procedure: A solution of 23.4 g (74.9 mmol) of boron tribromide-dimethyl sulfide complex in 150 mL of 1,2-dichloroethane was added dropwise to 3.00 g (15.0 mmol) of 2-methoxyphenyl phenyl ether in 50 mL dichloroethane at room temperature. The mixture was stirred at reflux overnight. 50 mL 3M NaOH was added to quench the reaction. After separation of layers, the organic layer was extracted with 3×100 mL 3M NaOH. The combined aqueous layer was acidified with conc. HCl, and the precipitated product was extracted with 3×150 mL ethyl ether. After washing with brine solution, drying over MgSO4, and filtering, solvents were evaporated under reduced pressure to give 2.30 g (82.4%) of an off-white solid, which was used without further purification. 1H NMR (300 MHz, CDCl3): δ 5.57 (s, 1H); 6.81-6.90 (m, 2H); 7.01-7.07 (m, 4H); 7.12 (t, 1H, J=7.3 Hz); 7.31-7.38 (m, 2H). ##STR105## at reflux overnight to quench the reaction After separation of layers the organic layer was extracted with 3×100 mL 3M NaOH the precipitated product was extracted with 3×150 mL ethyl ether After washing with brine solution drying over MgSO4 filtering solvents were evaporated under reduced pressure

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

Procedure: A solution of 23.4 g (74.9 mmol) of boron tribromide-dimethyl sulfide complex in 150 mL of 1,2-dichloroethane was added dropwise to 3.00 g (15.0 mmol) of 2-methoxyphenyl phenyl ether in 50 mL dichloroethane at room temperature. The mixture was stirred at reflux overnight. 50 mL 3M NaOH was added to quench the reaction. After separation of layers, the organic layer was extracted with 3×100 mL 3M NaOH. The combined aqueous layer was acidified with conc. HCl, and the precipitated product was extracted with 3×150 mL ethyl ether. After washing with brine solution, drying over MgSO4, and filtering, solvents were evaporated under reduced pressure to give 2.30 g (82.4%) of an off-white solid, which was used without further purification. 1H NMR (300 MHz, CDCl3): δ 5.57 (s, 1H); 6.81-6.90 (m, 2H); 7.01-7.07 (m, 4H); 7.12 (t, 1H, J=7.3 Hz); 7.31-7.38 (m, 2H). ##STR105## at reflux overnight to quench the reaction After separation of layers the organic layer was extracted with 3×100 mL 3M NaOH the precipitated product was extracted with 3×150 mL ethyl ether After washing with brine solution drying over MgSO4 filtering solvents were evaporated under reduced pressure

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

Procedure: With stirring, 11.5 g of chlorine are introduced at room temperature into a solution of 8 g of 2-phenoxyanisole in 85 ml of 1,2-dichloroethane in the course of 20 minutes. The reaction mixture is then stirred for 30 minutes at room temperature. The solvent is removed by evaporation and the crystalline residue is recrystallised from methanol, affording 4,5-dichloro-2-(4-chlorophenoxy)anisole in the form of white crystals with a melting point of 105°-106° C. The reaction mixture is then stirred for 30 minutes at room temperature The solvent is removed by evaporation the crystalline residue is recrystallised from methanol

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

Procedure: A mixture of 10 g of o-phenoxyanisol, 80 ml of hydroiodic acid (52%), 80 ml of acetic acid and 40 ml of acetic anhydride was refluxed for 1.5 hours. After being cooled, the reaction mixture was poured into ice-water to deposit a precipitate. The precipitate was dissolved in ether, and the solution was washed with an aqueous saturated sodium chloride solution, an aqueous saturated thiosulfuric acid aqueous solution and then an aqueous saturated sodium chloride solution. This ether solution was dried over anhydrous sodium sulfate, and the solvent was removed to give yellow solids. The solids were dissolved in acetic acid and stirred. The mixture was poured into cold water to deposit crystals. The crystals were washed with water and then with n-hexane, and dried at 80° C. under reduced pressure to obtain 7.8 g of o-phenoxyphenol as slightly yellow powders. was refluxed for 1.5 hours After being cooled the solution was washed with an aqueous saturated sodium chloride solution This ether solution was dried over anhydrous sodium sulfate the solvent was removed to give yellow solids The crystals were washed with water with n-hexane, and dried at 80° C. under reduced pressure

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

Procedure: A mixture of 10 g of o-phenoxyanisol, 80 ml of hydroiodic acid (52%), 80 ml of acetic acid and 40 ml of acetic anhydride was refluxed for 1.5 hours. After being cooled, the reaction mixture was poured into ice-water to deposit a precipitate. The precipitate was dissolved in ether, and the solution was washed with an aqueous saturated sodium chloride solution, an aqueous saturated thiosulfuric acid aqueous solution and then an aqueous saturated sodium chloride solution. This ether solution was dried over anhydrous sodium sulfate, and the solvent was removed to give yellow solids. The solids were dissolved in acetic acid and stirred. The mixture was poured into cold water to deposit crystals. The crystals were washed with water and then with n-hexane, and dried at 80° C. under reduced pressure to obtain 7.8 g of o-phenoxyphenol as slightly yellow powders. was refluxed for 1.5 hours After being cooled the solution was washed with an aqueous saturated sodium chloride solution This ether solution was dried over anhydrous sodium sulfate the solvent was removed to give yellow solids The crystals were washed with water with n-hexane, and dried at 80° C. under reduced pressure

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

Procedure: A solution of 23.4 g (74.9 mmol) of boron tribromide-dimethyl sulfide complex in 150 mL of 1,2-dichloroethane was added dropwise to 3.00 g (15.0 mmol) of 2-methoxyphenyl phenyl ether in 50 mL dichloroethane at room temperature. The mixture was stirred at reflux overnight. 50 mL 3M NaOH was added to quench the reaction. After separation of layers, the organic layer was extracted with 3×100 mL 3M NaOH. The combined aqueous layer was acidified with conc. HCl, and the precipitated product was extracted with 3×150 mL ethyl ether. After washing with brine solution, drying over MgSO4, and filtering, solvents were evaporated under reduced pressure to give 2.30 g (82.4%) of an off-white solid, which was used without further purification. 1H NMR (300 MHz, CDCl3): δ 5.57 (s, 1H); 6.81-6.90 (m, 2H); 7.01-7.07 (m, 4H); 7.12 (t, 1H, J=7.3 Hz); 7.31-7.38 (m, 2H). ##STR105## at reflux overnight to quench the reaction After separation of layers the organic layer was extracted with 3×100 mL 3M NaOH the precipitated product was extracted with 3×150 mL ethyl ether After washing with brine solution drying over MgSO4 filtering solvents were evaporated under reduced pressure

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

Procedure: With stirring, 11.5 g of chlorine are introduced at room temperature into a solution of 8 g of 2-phenoxyanisole in 85 ml of 1,2-dichloroethane in the course of 20 minutes. The reaction mixture is then stirred for 30 minutes at room temperature. The solvent is removed by evaporation and the crystalline residue is recrystallised from methanol, affording 4,5-dichloro-2-(4-chlorophenoxy)anisole in the form of white crystals with a melting point of 105°-106° C. The reaction mixture is then stirred for 30 minutes at room temperature The solvent is removed by evaporation the crystalline residue is recrystallised from methanol

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

Procedure: A mixture of 10 g of o-phenoxyanisol, 80 ml of hydroiodic acid (52%), 80 ml of acetic acid and 40 ml of acetic anhydride was refluxed for 1.5 hours. After being cooled, the reaction mixture was poured into ice-water to deposit a precipitate. The precipitate was dissolved in ether, and the solution was washed with an aqueous saturated sodium chloride solution, an aqueous saturated thiosulfuric acid aqueous solution and then an aqueous saturated sodium chloride solution. This ether solution was dried over anhydrous sodium sulfate, and the solvent was removed to give yellow solids. The solids were dissolved in acetic acid and stirred. The mixture was poured into cold water to deposit crystals. The crystals were washed with water and then with n-hexane, and dried at 80° C. under reduced pressure to obtain 7.8 g of o-phenoxyphenol as slightly yellow powders. was refluxed for 1.5 hours After being cooled the solution was washed with an aqueous saturated sodium chloride solution This ether solution was dried over anhydrous sodium sulfate the solvent was removed to give yellow solids The crystals were washed with water with n-hexane, and dried at 80° C. under reduced pressure