1-(chloromethyl)-2-phenoxybenzene

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

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

Procedure: Thionyl chloride (1.92 ml) was added in one portion to a solution of 2-phenoxybenzyl alcohol (4.80 g) in dry dichloromethane (50 ml). The resulting mixture was stirred at room temperature for 2 hours, then washed with water (×2), aqueous sodium bicarbonate (×2) and aqueous sodium chloride, dried and concentrated under reduced pressure to give 2-phenoxybenzyl chloride (4.87 g, 93%) as a colourless oil. washed with water (×2), aqueous sodium bicarbonate (×2) and aqueous sodium chloride dried concentrated under reduced pressure

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: Thionyl chloride (1.92 ml) was added in one portion to a solution of 2-phenoxybenzyl alcohol (4.80 g) in dry dichloromethane (50 ml). The resulting mixture was stirred at room temperature for 2 hours, then washed with water (×2), aqueous sodium bicarbonate (×2) and aqueous sodium chloride, dried and concentrated under reduced pressure to give 2-phenoxybenzyl chloride (4.87 g, 93%) as a colourless oil. washed with water (×2), aqueous sodium bicarbonate (×2) and aqueous sodium chloride dried concentrated under reduced pressure

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

Procedure: Thionyl chloride (1.92 ml) was added in one portion to a solution of 2-phenoxybenzyl alcohol (4.80 g) in dry dichloromethane (50 ml). The resulting mixture was stirred at room temperature for 2 hours, then washed with water (×2), aqueous sodium bicarbonate (×2) and aqueous sodium chloride, dried and concentrated under reduced pressure to give 2-phenoxybenzyl chloride (4.87 g, 93%) as a colourless oil. washed with water (×2), aqueous sodium bicarbonate (×2) and aqueous sodium chloride dried concentrated under reduced pressure

Conditions: temp:40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 7.82 g (3.58 mmol) of o-phenoxybenzyl chloride dissolved in 8 ml of dimethoxyethane were added dropwise at room temperature to a solution of 8.82 g (35.8 mmol) of (E)-4-(3-phenyl-2-propenyl)-1-piperazineethanol and 4.42 g (39.4 mmol) of potassium tert-butyloxide and 4 g of 3A molecular sieve in 125 ml of dry dimethoxyethane. After stirring for 3 days at 40° C., the mixture was cooled to room temperature. The salts in the solution were filtered off and the solution was evaporated. The residue obtained was purified by means of column chromatography over silica (eluent toluene:ethanol=9:1). The collected fractions were dissolved in ethanol and 5 ml of 4.9 N HCl in ethanol was added. The clearsolution was evaporated. Yield 2.4 g (13%), m.p. 221° C. the mixture was cooled to room temperature The salts in the solution were filtered off the solution was evaporated The residue obtained was purified by means of column chromatography over silica (eluent toluene:ethanol=9:1) The collected fractions were dissolved in ethanol 5 ml of 4.9 N HCl in ethanol was added The clearsolution was evaporated

Conditions: temp:40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 7.82 g (3.58 mmol) of o-phenoxybenzyl chloride dissolved in 8 ml of dimethoxyethane were added dropwise at room temperature to a solution of 8.82 g (35.8 mmol) of (E)-4-(3-phenyl-2-propenyl)-1-piperazineethanol and 4.42 g (39.4 mmol) of potassium tert-butyloxide and 4 g of 3A molecular sieve in 125 ml of dry dimethoxyethane. After stirring for 3 days at 40° C., the mixture was cooled to room temperature. The salts in the solution were filtered off and the solution was evaporated. The residue obtained was purified by means of column chromatography over silica (eluent toluene:ethanol=9:1). The collected fractions were dissolved in ethanol and 5 ml of 4.9 N HCl in ethanol was added. The clearsolution was evaporated. Yield 2.4 g (13%), m.p. 221° C. the mixture was cooled to room temperature The salts in the solution were filtered off the solution was evaporated The residue obtained was purified by means of column chromatography over silica (eluent toluene:ethanol=9:1) The collected fractions were dissolved in ethanol 5 ml of 4.9 N HCl in ethanol was added The clearsolution was evaporated

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

Procedure: Thionyl chloride (1.92 ml) was added in one portion to a solution of 2-phenoxybenzyl alcohol (4.80 g) in dry dichloromethane (50 ml). The resulting mixture was stirred at room temperature for 2 hours, then washed with water (×2), aqueous sodium bicarbonate (×2) and aqueous sodium chloride, dried and concentrated under reduced pressure to give 2-phenoxybenzyl chloride (4.87 g, 93%) as a colourless oil. washed with water (×2), aqueous sodium bicarbonate (×2) and aqueous sodium chloride dried concentrated under reduced pressure

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

Procedure: Thionyl chloride (1.92 ml) was added in one portion to a solution of 2-phenoxybenzyl alcohol (4.80 g) in dry dichloromethane (50 ml). The resulting mixture was stirred at room temperature for 2 hours, then washed with water (×2), aqueous sodium bicarbonate (×2) and aqueous sodium chloride, dried and concentrated under reduced pressure to give 2-phenoxybenzyl chloride (4.87 g, 93%) as a colourless oil. washed with water (×2), aqueous sodium bicarbonate (×2) and aqueous sodium chloride dried concentrated under reduced pressure

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

Procedure: Into a three-necked 300 ml round-bottom flask are charged 7.4 g (0.15 mole) of sodium cyanide and 80 ml of dimethyl sulfoxide. To this slurry is added 30 g (0.13 mole) of 2-phenoxybenzyl chloride dropwise. Reaction temperature increases from 24° to 44° C. The reaction mixture is stirred for an additional 11/2 hours. To this reaction mixture is added 13.7 g (0.13 mole) of butyl chloride followed by dropwise addition of 34 g (0.4 mole) of 50% sodium hydroxide solution. After stirring for an additional 1/2 hour, reaction mixture is poured into 150 ml of water and extracted with hexane. The combined hexane extracts are washed with water and dried over MgSO4. Solvent is evaporated to give 32 g of crude product. Material can be further purified by vacuum distillation (bp 149-60/0.25 mm). Reaction temperature increases from 24° to 44° C After stirring for an additional 1/2 hour reaction mixture extracted with hexane The combined hexane extracts are washed with water dried over MgSO4 Solvent is evaporated

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

Procedure: Into a three-necked 500 ml round-bottom flask are charged 25 g (0.125 mole) of o-phenoxy benzyl alcohol and 200 ml of benzene. To this solution is added 18 g (0.15 mole) of thionyl chloride dropwise with stirring. The reaction mixture is then heated to reflux for four hours. Solvent and excess thionyl chloride are removed under vacuum to give 30 g of product. The reaction mixture is then heated to reflux for four hours Solvent and excess thionyl chloride are removed under vacuum