2-(2-methoxyphenoxy)acetonitrile

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

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

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

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 the 2-cyanomethoxyanisole (5.6 g, 0.034 mol) in anhydrous ammonia (25 ml) and ethanol (50 ml) was heated to 120° C. at 500 psi for 12 h in the presence of raney nickel (1.4 g). The reaction mixture was filtered, concentrated under reduced pressure, the residue taken up in ether, and washed with 1.2 M HCl. The acidic phase was then rendered basic (pH=12) with careful addition of solid KOH and the alkaline solution extracted with ether. The organic phase was dried (MgSO4) and concentrated under reduced pressure to give the product (1.99 g, 35%) as an oil. IR. NMR. MS. The reaction mixture was filtered concentrated under reduced pressure washed with 1.2 M HCl with careful addition of solid KOH the alkaline solution extracted with ether The organic phase was dried (MgSO4) concentrated under reduced pressure

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

Procedure: A solution of the 2-cyanomethoxyanisole (5.6 g, 0.034 mol) in anhydrous ammonia (25 ml) and ethanol (50 ml) was heated to 120° C. at 500 psi for 12 h in the presence of raney nickel (1.4 g). The reaction mixture was filtered, concentrated under reduced pressure, the residue taken up in ether, and washed with 1.2 M HCl. The acidic phase was then rendered basic (pH=12) with careful addition of solid KOH and the alkaline solution extracted with ether. The organic phase was dried (MgSO4) and concentrated under reduced pressure to give the product (1.99 g, 35%) as an oil. IR. NMR. MS. The reaction mixture was filtered concentrated under reduced pressure washed with 1.2 M HCl with careful addition of solid KOH the alkaline solution extracted with ether The organic phase was dried (MgSO4) concentrated under reduced pressure

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

Procedure: A solution of the 2-cyanomethoxyanisole (5.6 g, 0.034 mol) in anhydrous ammonia (25 ml) and ethanol (50 ml) was heated to 120° C. at 500 psi for 12 h in the presence of raney nickel (1.4 g). The reaction mixture was filtered, concentrated under reduced pressure, the residue taken up in ether, and washed with 1.2 M HCl. The acidic phase was then rendered basic (pH=12) with careful addition of solid KOH and the alkaline solution extracted with ether. The organic phase was dried (MgSO4) and concentrated under reduced pressure to give the product (1.99 g, 35%) as an oil. IR. NMR. MS. The reaction mixture was filtered concentrated under reduced pressure washed with 1.2 M HCl with careful addition of solid KOH the alkaline solution extracted with ether The organic phase was dried (MgSO4) concentrated under reduced pressure

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

Procedure: Potassium carbonate (24 g) was added to a solution of of 2-methoxy phenol (18.94 g, 0.152 mol) in acetone (500 ml) at room temperature. A solution of bromoacetonitrile (17.43 g, 0.145 mol) in acetone (500 ml) was then added and the resulting suspension was heated at reflux for 10 h. The reaction vessel was then cooled and the solution was concentrated under reduced pressure and taken up into water (150 ml). Chloroform (250 ml) was added and the two layers separated. The organic phase was washed with brine (100 ml) and 10% aqueous NaOH (100 ml). The organic phase was dried (MgSO4) and concentrated under reduced pressure to give the product (19.91 g, 80%) as an oil. 1H NMR (CDCl3, 250 MHz) 7.0 (4H m), 4.8 (2H, s), 3.9 (3H, s). the resulting suspension was heated at reflux for 10 h The reaction vessel was then cooled the solution was concentrated under reduced pressure Chloroform (250 ml) was added the two layers separated The organic phase was washed with brine (100 ml) and 10% aqueous NaOH (100 ml) The organic phase was dried (MgSO4) concentrated under reduced pressure

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

Procedure: Potassium carbonate (24 g) was added to a solution of of 2-methoxy phenol (18.94 g, 0.152 mol) in acetone (500 ml) at room temperature. A solution of bromoacetonitrile (17.43 g, 0.145 mol) in acetone (500 ml) was then added and the resulting suspension was heated at reflux for 10 h. The reaction vessel was then cooled and the solution was concentrated under reduced pressure and taken up into water (150 ml). Chloroform (250 ml) was added and the two layers separated. The organic phase was washed with brine (100 ml) and 10% aqueous NaOH (100 ml). The organic phase was dried (MgSO4) and concentrated under reduced pressure to give the product (19.91 g, 80%) as an oil. 1H NMR (CDCl3, 250 MHz) 7.0 (4H m), 4.8 (2H, s), 3.9 (3H, s). the resulting suspension was heated at reflux for 10 h The reaction vessel was then cooled the solution was concentrated under reduced pressure Chloroform (250 ml) was added the two layers separated The organic phase was washed with brine (100 ml) and 10% aqueous NaOH (100 ml) The organic phase was dried (MgSO4) concentrated under reduced pressure

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

Procedure: A solution of the 2-cyanomethoxyanisole (5.6 g, 0.034 mol) in anhydrous ammonia (25 ml) and ethanol (50 ml) was heated to 120° C. at 500 psi for 12 h in the presence of raney nickel (1.4 g). The reaction mixture was filtered, concentrated under reduced pressure, the residue taken up in ether, and washed with 1.2 M HCl. The acidic phase was then rendered basic (pH=12) with careful addition of solid KOH and the alkaline solution extracted with ether. The organic phase was dried (MgSO4) and concentrated under reduced pressure to give the product (1.99 g, 35%) as an oil. IR. NMR. MS. The reaction mixture was filtered concentrated under reduced pressure washed with 1.2 M HCl with careful addition of solid KOH the alkaline solution extracted with ether The organic phase was dried (MgSO4) concentrated under reduced pressure

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

Procedure: Potassium carbonate (24 g) was added to a solution of of 2-methoxy phenol (18.94 g, 0.152 mol) in acetone (500 ml) at room temperature. A solution of bromoacetonitrile (17.43 g, 0.145 mol) in acetone (500 ml) was then added and the resulting suspension was heated at reflux for 10 h. The reaction vessel was then cooled and the solution was concentrated under reduced pressure and taken up into water (150 ml). Chloroform (250 ml) was added and the two layers separated. The organic phase was washed with brine (100 ml) and 10% aqueous NaOH (100 ml). The organic phase was dried (MgSO4) and concentrated under reduced pressure to give the product (19.91 g, 80%) as an oil. 1H NMR (CDCl3, 250 MHz) 7.0 (4H m), 4.8 (2H, s), 3.9 (3H, s). the resulting suspension was heated at reflux for 10 h The reaction vessel was then cooled the solution was concentrated under reduced pressure Chloroform (250 ml) was added the two layers separated The organic phase was washed with brine (100 ml) and 10% aqueous NaOH (100 ml) The organic phase was dried (MgSO4) concentrated under reduced pressure

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 2-(2-methoxy-phenoxy)acetonitrile (5 g, 31 mmol) in anhydrous ethyl ether (100 ml) was added lithium aluminum hydride (1.6 g, 40 mmol) portionwise. The reaction mixture was heated to reflux for 3 hours and then cooled to 0° C. The reaction was quenched with 1N hydrochloric acid and diluted with water (PH=1, aqueous layer). The mixture was extracted with ethyl acetate (3×150 ml), neutralized with 50% sodium hydroxide to pH>10, and extracted again with more ethyl acetate (3×100 ml). The combined organic layers were washed with brine (3×150 ml), dried over anhydrous sodium sulfate and filtered. The solvent was removed under vacuum to afford 2.85 g (56%) of product as an oil; MS EI m/e 167 (M+). The reaction mixture was heated to reflux for 3 hours The reaction was quenched with 1N hydrochloric acid diluted with water (PH=1, aqueous layer) The mixture was extracted with ethyl acetate (3×150 ml) extracted again with more ethyl acetate (3×100 ml) The combined organic layers were washed with brine (3×150 ml) dried over anhydrous sodium sulfate filtered The solvent was removed under vacuum