1-(2-chloroethoxy)-2-methoxybenzene

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 52.88 g (0.426 mol) of guaiacol (34), 50 ml (0.426 mol) of 1,2-dichloroethane, 88.3 g (0.639 mol) of potassium hydroxide and heated at reflux for 24 h. The mixture was concentrated and extracted into ethyl acetate and evaporate the solvent and purified by column chromatography to gave 41.47 g (52%) of 1-(2-Chloroethoxy)-2-methoxy benzene (35) as a white solid, mp 42-43° C. heated at reflux for 24 h The mixture was concentrated extracted into ethyl acetate evaporate the solvent purified by column chromatography

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

Procedure: To a solution of 2-methoxyphenol (14.4 g, 116 mmol) in 2-butanone (200 mL) was added bromochloroethane (69.0 g, 480 mmol) followed by the addition of potassium carbonate (40.0 g, 280 mmol). The reaction mixture was mechanically stirred and heated to reflux for 24 h, then cooled to room temperature. The solids were filtered off and the solvent was removed under vacuum. The residue was dissolved in diethyl ether and washed with 10% of NaOH, dried over anhydrous magnesium sulfate, filtered and concentrated. Purification by silica gel column chromatography (25% EtOAc/hexane) afforded 7.55 g (35%) of a solid: mp 36-38°C. (Lit.2 41-43° C,); 1H NMR (DMSO, 400 MHz), 3.75 (s, 3H), 3.91 (dd, 2H), 4.20 (dd, 2H), 6.86-6.99 (m, 4H); MS (EI) m/z 186 (M+). heated to reflux for 24 h The solids were filtered off the solvent was removed under vacuum The residue was dissolved in diethyl ether washed with 10% of NaOH dried over anhydrous magnesium sulfate filtered concentrated Purification by silica gel column chromatography (25% EtOAc/hexane)

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

Procedure: A mixture of 52.88 g (0.426 mole) of guaiacol, 100 g (0.426 mole) of chloroethyl tosylate, 88.3 g (0.639 mole) of powdered potassium carbonate and 600 mL of 2-butanone is stirred mechanically and refluxed for 2 days. The reaction is filtered and the solid is rinsed with 2-butanone. The filtrate is evaporated and the residue taken up in ether and washed with 1N NaOH to remove unreacted guaiacol. The ether layer is dried over sodium sulfate, filtered and evaporated to give an oil which slowly crystallized. The solid is isolated with cold cyclohexane to give 41.47 g (52%) of 1-(2-Chloroethoxy)-2-methoxybenzene as a white solid, m.p. 42-3° C. refluxed for 2 days The reaction is filtered the solid is rinsed with 2-butanone The filtrate is evaporated washed with 1N NaOH to remove unreacted guaiacol The ether layer is dried over sodium sulfate filtered evaporated to give an oil which slowly crystallized The solid is isolated with cold cyclohexane

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Then 25.1 g of 2-(o-methoxyphenoxy) ethyl chloride, 33.40 g of potassium methacrylate, 11.17 g of potassium iodide, 50 ml of N,N-dimethylformamide, and a small amount of hydroquinone were placed in a 200 ml-flask equipped with a stirring device and a cooling pipe. The mixture was heated at 100° C. and stirred. The reacted mixture was refined by column chromatography using silica gel, and 24.8 g of 2-(o-methoxyphenoxy)ethyl methacrylate was produced. equipped with a stirring device

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

Procedure: 24.83 g (0.2 mole) of o-methoxyphenol and 100 ml of tetrahydrofuran were placed in a 500 ml-flask equipped with a stirring device and a cooling pipe. A solution in which sodium methoxide (0.2 mole) was dissolved in methanol was added to the flask while stirring the contents. Then tetrahydrofuran and methanol were eliminated at reduced pressure. 300 ml of tetrahydrofuran was added to the flask and then 46.94 g (0.2 mole) of 2-chloroethyl-p-toluene sulfonate was added thereto. The mixture was then stirred under heating reflux for 20 hours to promote reaction. After reaction, insoluble matters were eliminated by filtration, and the product was condensed at reduced pressure. The reaction mixture was then refined by column chromatography using silica gel, and 25.1 g of 2-(o-methoxyphenoxy)ethyl chloride was produced. equipped with a stirring device was added to the flask The mixture was then stirred under heating reflux for 20 hours reaction After reaction, insoluble matters were eliminated by filtration condensed at reduced pressure

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

Procedure: 24.83 g (0.2 mole) of o-methoxyphenol and 100 ml of tetrahydrofuran were placed in a 500 ml-flask equipped with a stirring device and a cooling pipe. A solution in which sodium methoxide (0.2 mole) was dissolved in methanol was added to the flask while stirring the contents. Then tetrahydrofuran and methanol were eliminated at reduced pressure. 300 ml of tetrahydrofuran was added to the flask and then 46.94 g (0.2 mole) of 2-chloroethyl-p-toluene sulfonate was added thereto. The mixture was then stirred under heating reflux for 20 hours to promote reaction. After reaction, insoluble matters were eliminated by filtration, and the product was condensed at reduced pressure. The reaction mixture was then refined by column chromatography using silica gel, and 25.1 g of 2-(o-methoxyphenoxy)ethyl chloride was produced. equipped with a stirring device was added to the flask The mixture was then stirred under heating reflux for 20 hours reaction After reaction, insoluble matters were eliminated by filtration condensed at reduced pressure

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

Procedure: A mixture of 52.88 g (0.426 mol) of guaiacol (34), 50 ml (0.426 mol) of 1,2-dichloroethane, 88.3 g (0.639 mol) of potassium hydroxide and heated at reflux for 24 h. The mixture was concentrated and extracted into ethyl acetate and evaporate the solvent and purified by column chromatography to gave 41.47 g (52%) of 1-(2-Chloroethoxy)-2-methoxy benzene (35) as a white solid, mp 42-43° C. heated at reflux for 24 h The mixture was concentrated extracted into ethyl acetate evaporate the solvent purified by column chromatography

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

Procedure: To a solution of 2-methoxyphenol (14.4 g, 116 mmol) in 2-butanone (200 mL) was added bromochloroethane (69.0 g, 480 mmol) followed by the addition of potassium carbonate (40.0 g, 280 mmol). The reaction mixture was mechanically stirred and heated to reflux for 24 h, then cooled to room temperature. The solids were filtered off and the solvent was removed under vacuum. The residue was dissolved in diethyl ether and washed with 10% of NaOH, dried over anhydrous magnesium sulfate, filtered and concentrated. Purification by silica gel column chromatography (25% EtOAc/hexane) afforded 7.55 g (35%) of a solid: mp 36-38°C. (Lit.2 41-43° C,); 1H NMR (DMSO, 400 MHz), 3.75 (s, 3H), 3.91 (dd, 2H), 4.20 (dd, 2H), 6.86-6.99 (m, 4H); MS (EI) m/z 186 (M+). heated to reflux for 24 h The solids were filtered off the solvent was removed under vacuum The residue was dissolved in diethyl ether washed with 10% of NaOH dried over anhydrous magnesium sulfate filtered concentrated Purification by silica gel column chromatography (25% EtOAc/hexane)

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

Procedure: To a solution of 2-methoxyphenol (14.4 g, 116 mmol) in 2-butanone (200 mL) was added bromochloroethane (69.0 g, 480 mmol) followed by the addition of potassium carbonate (40.0 g, 280 mmol). The reaction mixture was mechanically stirred and heated to reflux for 24 h, then cooled to room temperature. The solids were filtered off and the solvent was removed under vacuum. The residue was dissolved in diethyl ether and washed with 10% of NaOH, dried over anhydrous magnesium sulfate, filtered and concentrated. Purification by silica gel column chromatography (25% EtOAc/hexane) afforded 7.55 g (35%) of a solid: mp 36-38°C. (Lit.2 41-43° C,); 1H NMR (DMSO, 400 MHz), 3.75 (s, 3H), 3.91 (dd, 2H), 4.20 (dd, 2H), 6.86-6.99 (m, 4H); MS (EI) m/z 186 (M+). heated to reflux for 24 h The solids were filtered off the solvent was removed under vacuum The residue was dissolved in diethyl ether washed with 10% of NaOH dried over anhydrous magnesium sulfate filtered concentrated Purification by silica gel column chromatography (25% EtOAc/hexane)

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 52.88 g (0.426 mole) of guaiacol, 100 g (0.426 mole) of chloroethyl tosylate, 88.3 g (0.639 mole) of powdered potassium carbonate and 600 mL of 2-butanone is stirred mechanically and refluxed for 2 days. The reaction is filtered and the solid is rinsed with 2-butanone. The filtrate is evaporated and the residue taken up in ether and washed with 1N NaOH to remove unreacted guaiacol. The ether layer is dried over sodium sulfate, filtered and evaporated to give an oil which slowly crystallized. The solid is isolated with cold cyclohexane to give 41.47 g (52%) of 1-(2-Chloroethoxy)-2-methoxybenzene as a white solid, m.p. 42–3° C. refluxed for 2 days The reaction is filtered the solid is rinsed with 2-butanone The filtrate is evaporated washed with 1N NaOH to remove unreacted guaiacol The ether layer is dried over sodium sulfate filtered evaporated to give an oil which slowly crystallized The solid is isolated with cold cyclohexane