2-(4-ethoxyphenyl)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:25.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1.6M n-Butyllithium (680 ml) is added over 5 min to a stirred solution of 4-ethoxyphenyl acetonitrile (56 g) in anhydrous THF (600 ml) at 25° C. under an atmosphere of nitrogen. After 1 h, a solution of 1.2 dichloroethane (111 g) in anhydrous THF (300 ml) is added dropwise over 2 h and the mixture stirred at 25° C. for 16 h. The mixture is then poured onto 3N HCl (1 l ), concentrated under reduced pressure, extracted with diethyl ether (x3), washed with water, dried over anhydrous sodium sulphate, the solvent removed under reduced pressure and the residue distilled to give the product, b.p. 116°-120° C., yield 40 g. nD 1.5320. concentrated under reduced pressure extracted with diethyl ether (x3) washed with water dried over anhydrous sodium sulphate the solvent removed under reduced pressure the residue distilled to give the product, b.p. 116°-120° C., yield 40 g

Conditions: temp:25.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1.6M n-Butyllithium (680 ml) is added over 5 min to a stirred solution of 4-ethoxyphenyl acetonitrile (56 g) in anhydrous THF (600 ml) at 25° C. under an atmosphere of nitrogen. After 1 h, a solution of 1.2 dichloroethane (111 g) in anhydrous THF (300 ml) is added dropwise over 2 h and the mixture stirred at 25° C. for 16 h. The mixture is then poured onto 3N HCl (1 l ), concentrated under reduced pressure, extracted with diethyl ether (x3), washed with water, dried over anhydrous sodium sulphate, the solvent removed under reduced pressure and the residue distilled to give the product, b.p. 116°-120° C., yield 40 g. nD 1.5320. concentrated under reduced pressure extracted with diethyl ether (x3) washed with water dried over anhydrous sodium sulphate the solvent removed under reduced pressure the residue distilled to give the product, b.p. 116°-120° C., yield 40 g

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

Procedure: To 7.5 ml (0.012 mol) of 1.7M n-butyllithium in hexane, at room temperature, under an atmosphere of nitrogen, is added rapidly 10 ml of anhydrous tetrahydrofuran, followed by a solution of 4-ethoxyphenyl acetonitrile (0.8 g 0.005 mol) in 4 ml of tetrahydrofuran, during 5 minutes. The reaction mixture is stirred magnetically for 1 hour then treated with 0.50 g (0.005 mol) of 1,2-dichloroethane in 10 ml of tetrahydrofuran, during a period of 40 minutes (slow addition is important). After 16 hours, the mixture is hydrolysed by 10 ml of 3N HCl and then taken up in ether, washed with water, sodium bicarbonate, water and dried over anhydrous sodium sulphate. The solvent is removed under reduced pressure. Yield: 0.64 g of a viscous semi-crystalline oil. (slow addition is important) After 16 hours washed with water, sodium bicarbonate, water dried over anhydrous sodium sulphate The solvent is removed under reduced pressure

Conditions: temp:-20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 8.8 g of diisopropylamine in 150 ml of dry tetrahydrofuran were added 50 ml (1.5 mmole/ml) of n-butyl lithium at -50° C. After stirring at -20° C. for 30 minutes, 10.0 g of 4-ethoxyphenylacetonitrile was added thereto at -50° C. After stirring at the same temperature for 1 hour, 10.1 g of methyl iodide was added dropwise at -50° C. After stirring at the same temperature for 3 hours and then at 20° C. for 10 hours, the reaction solution was poured into 10% aqueous hydrochloric acid and extracted with ethyl acetate. After concentrating the ethyl acetate layer, the residual oil was column-chromatographed on silica gel (developing solvent, n-hexane: ethyl acetate=20:1) to obtain 9.50 g of the desired 2-(4-ethoxyphenyl) propionitrile [corresponding to the compound represented by the foregoing formula (II) wherein R1 is an ethoxy group, R2 is a hydrogen atom and R4 is a methyl group] as a pale yellow oil. at -50° C After stirring at the same temperature for 1 hour After stirring at the same temperature for 3 hours at 20° C. for 10 hours extracted with ethyl acetate After concentrating the ethyl acetate layer the residual oil was column-chromatographed on silica gel (developing solvent, n-hexane: ethyl acetate=20:1)

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

Procedure: To 7.5 ml (0.012 mol) of 1.7M n-butyllithium in hexane, at room temperature, under an atmosphere of nitrogen, is added rapidly 10 ml of anhydrous tetrahydrofuran, followed by a solution of 4-ethoxyphenyl acetonitrile (0.8 g 0.005 mol) in 4 ml of tetrahydrofuran, during 5 minutes. The reaction mixture is stirred magnetically for 1 hour then treated with 0.50 g (0.005 mol) of 1,2-dichloroethane in 10 ml of tetrahydrofuran, during a period of 40 minutes (slow addition is important). After 16 hours, the mixture is hydrolysed by 10 ml of 3N HCl and then taken up in ether, washed with water, sodium bicarbonate, water and dried over anhydrous sodium sulphate. The solvent is removed under reduced pressure. Yield: 0.64 g of a viscous semi-crystalline oil. (slow addition is important) After 16 hours washed with water, sodium bicarbonate, water dried over anhydrous sodium sulphate The solvent is removed under reduced pressure

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

Procedure: To 7.5 ml (0.012 mol) of 1.7M n-butyllithium in hexane, at room temperature, under an atmosphere of nitrogen, is added rapidly 10 ml of anhydrous tetrahydrofuran, followed by a solution of 4-ethoxyphenyl acetonitrile (0.8 g 0.005 mol) in 4 ml of tetrahydrofuran, during 5 minutes. The reaction mixture is stirred magnetically for 1 hour then treated with 0.50 g (0.005 mol) of 1,2-dichloroethane in 10 ml of tetrahydrofuran, during a period of 40 minutes (slow addition is important). After 16 hours, the mixture is hydrolysed by 10 ml of 3N HCl and then taken up in ether, washed with water, sodium bicarbonate, water and dried over anhydrous sodium sulphate. The solvent is removed under reduced pressure. Yield: 0.64 g of a viscous semi-crystalline oil. (slow addition is important) After 16 hours washed with water, sodium bicarbonate, water dried over anhydrous sodium sulphate The solvent is removed under reduced pressure

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

Procedure: 2 g of KOH were dissolved in 30 ml of methanol whilst being heated. The solution was cooled down to room temperature, after which 3.3 g of p-ethoxybenzylcyanide and 4 g of p-hexyloxybenzaldehyde were added. The mixture was stirred and subsequently stored at room temperature for 1 hour and then at -25° C for 2 hours. The crystallisate was filtered off and subsequently recrystallized from methanol and petroleum ether (60-80). Melting point 53.5°-54° C. Transition point nematic-isotropic 80° C. In a similar way the following compounds were obtained: whilst being heated at -25° C for 2 hours The crystallisate was filtered off subsequently recrystallized from methanol and petroleum ether (60-80) Transition point nematic-isotropic 80° C In a similar way the following compounds were obtained

Conditions: temp:25.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1.6M n-Butyllithium (680 ml) is added over 5 min to a stirred solution of 4-ethoxyphenyl acetonitrile (56 g) in anhydrous THF (600 ml) at 25° C. under an atmosphere of nitrogen. After 1 h, a solution of 1.2 dichloroethane (111 g) in anhydrous THF (300 ml) is added dropwise over 2 h and the mixture stirred at 25° C. for 16 h. The mixture is then poured onto 3N HCl (1 l ), concentrated under reduced pressure, extracted with diethyl ether (x3), washed with water, dried over anhydrous sodium sulphate, the solvent removed under reduced pressure and the residue distilled to give the product, b.p. 116°-120° C., yield 40 g. nD 1.5320. concentrated under reduced pressure extracted with diethyl ether (x3) washed with water dried over anhydrous sodium sulphate the solvent removed under reduced pressure the residue distilled to give the product, b.p. 116°-120° C., yield 40 g