2-(2-hydroxyphenyl)acetonitrile

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

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

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: (2-Hydro xyphenyl)acetonitrile (1.01 g, 0.0076 mol) was dissolved in DMF (10 ml), and to this solution were successively added benzyl bromide (0.90 ml, 0.0076 mol, 1.0 eq) and anhydrous potassium carbonate (2.1 g, 0.015 mol, 3.0 eq). The mixture was stirred with heating at 90° C. for 1.5 hours. The reaction mixture was cooled to room temperature, and water (10 ml) was added. The mixture was extracted twice with ethyl acetate (30 ml). The organic layers were combined, washed with saturated brine (60 ml) and dried over anhydrous sodium sulfate. The drying agent was filtered off, and the filtrate was concentrated under reduced pressure to give (2-benzyloxyphenyl)acetonitrile (2.04 g, 100%) as a colorless solid. The reaction mixture was cooled to room temperature The mixture was extracted twice with ethyl acetate (30 ml) washed with saturated brine (60 ml) dried over anhydrous sodium sulfate The drying agent was filtered off the filtrate was concentrated under reduced pressure

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: (2-Hydro xyphenyl)acetonitrile (1.01 g, 0.0076 mol) was dissolved in DMF (10 ml), and to this solution were successively added benzyl bromide (0.90 ml, 0.0076 mol, 1.0 eq) and anhydrous potassium carbonate (2.1 g, 0.015 mol, 3.0 eq). The mixture was stirred with heating at 90° C. for 1.5 hours. The reaction mixture was cooled to room temperature, and water (10 ml) was added. The mixture was extracted twice with ethyl acetate (30 ml). The organic layers were combined, washed with saturated brine (60 ml) and dried over anhydrous sodium sulfate. The drying agent was filtered off, and the filtrate was concentrated under reduced pressure to give (2-benzyloxyphenyl)acetonitrile (2.04 g, 100%) as a colorless solid. The reaction mixture was cooled to room temperature The mixture was extracted twice with ethyl acetate (30 ml) washed with saturated brine (60 ml) dried over anhydrous sodium sulfate The drying agent was filtered off the filtrate was concentrated under reduced pressure

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

Procedure: To a mixture of 2.92 g of (2-hydroxyphenyl)acetonitrile, 4.71 g of tert-butyl bromoacetate and 110 mL of DMF was added 6.06 g of potassium carbonate at room temperature, followed by stirring for 12 hours. To the reaction solution was added water, followed by extraction with ethyl acetate. The extract was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography using hexane/ethyl acetate as an eluent solvent to obtain 5.29 g of tert-butyl[2-(cyanomethyl)phenoxy]acetate as a yellow oily substance. followed by extraction with ethyl acetate The extract was dried over anhydrous magnesium sulfate concentrated under reduced pressure The residue was purified by silica gel column chromatography

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: The title compound was prepared from 2-hydroxy-benzeneacetonitrile (J. Org. Chem.; 66, 3435; 2001) and 1-(3-chloropropyl)pyrrolidine, using a method similar to that of preparation 104, as a pale brown gum in 58% yield. 1H NMR (400 MHz, CD3OD) δ: 7.33-7.25 (2H, m), 7.02-6.90 (2H, m), 4.12-4.09 (2H, m), 3.75 (2H, s), 2.76-2.72 (2H, m), 2.62-2.57 (4H, m), 2.09-2.02 (2H, m), 1.87-1.78 (4H, m); LRMS APCI m/z 245 [M+H]+ of preparation 104

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

Procedure: To a mixture of 2.92 g of (2-hydroxyphenyl)acetonitrile, 4.71 g of tert-butyl bromoacetate and 110 mL of DMF was added 6.06 g of potassium carbonate at room temperature, followed by stirring for 12 hours. To the reaction solution was added water, followed by extraction with ethyl acetate. The extract was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography using hexane/ethyl acetate as an eluent solvent to obtain 5.29 g of tert-butyl[2-(cyanomethyl)phenoxy]acetate as a yellow oily substance. followed by extraction with ethyl acetate The extract was dried over anhydrous magnesium sulfate concentrated under reduced pressure The residue was purified by silica gel column chromatography

Conditions: temp:125.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 29.8g of 2-hydroxybenzyl alcohol are dissolved in 250 ml of dimethylsulfoxide, together with 18g of potassium cyanide, and the mixture is heated to 125°C. 16g of glacial acetic acid are then added dropwise over the course of 1 hour and the mixture is stirred for a further 2 hours at 125°C. The dimethylsulfoxide is removed in vacuo and the residue is stirred with 200 ml of water and 150 ml of chloroform. The chloroform phase is separated off and the aqueous phase is re-extracted with 150 ml of chloroform. The combined chloroform phases are extracted by shaking with water and dried with sodium sulfate. After distilling off the chloroform, an oil remains, which solidifies on cooling. Yield: 19.8g = 60.5% of theory. Recrystallization from benzene/ligroin: melting point 118°C. The dimethylsulfoxide is removed in vacuo the residue is stirred with 200 ml of water and 150 ml of chloroform The chloroform phase is separated off the aqueous phase is re-extracted with 150 ml of chloroform The combined chloroform phases are extracted by shaking with water dried with sodium sulfate After distilling off the chloroform on cooling Recrystallization from benzene/ligroin

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: (2-Hydro xyphenyl)acetonitrile (1.01 g, 0.0076 mol) was dissolved in DMF (10 ml), and to this solution were successively added benzyl bromide (0.90 ml, 0.0076 mol, 1.0 eq) and anhydrous potassium carbonate (2.1 g, 0.015 mol, 3.0 eq). The mixture was stirred with heating at 90° C. for 1.5 hours. The reaction mixture was cooled to room temperature, and water (10 ml) was added. The mixture was extracted twice with ethyl acetate (30 ml). The organic layers were combined, washed with saturated brine (60 ml) and dried over anhydrous sodium sulfate. The drying agent was filtered off, and the filtrate was concentrated under reduced pressure to give (2-benzyloxyphenyl)acetonitrile (2.04 g, 100%) as a colorless solid. The reaction mixture was cooled to room temperature The mixture was extracted twice with ethyl acetate (30 ml) washed with saturated brine (60 ml) dried over anhydrous sodium sulfate The drying agent was filtered off the filtrate was concentrated under reduced pressure

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

Procedure: To a mixture of 2.92 g of (2-hydroxyphenyl)acetonitrile, 4.71 g of tert-butyl bromoacetate and 110 mL of DMF was added 6.06 g of potassium carbonate at room temperature, followed by stirring for 12 hours. To the reaction solution was added water, followed by extraction with ethyl acetate. The extract was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography using hexane/ethyl acetate as an eluent solvent to obtain 5.29 g of tert-butyl[2-(cyanomethyl)phenoxy]acetate as a yellow oily substance. followed by extraction with ethyl acetate The extract was dried over anhydrous magnesium sulfate concentrated under reduced pressure The residue was purified by silica gel column chromatography