2-(4-chlorophenoxy)-1-phenylethanone

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Bromine (11.6g) in chloroform (40ml) was added dropwise to a stirred solution of 4-chloro-α-phenoxyacetophenone (18.8g) in chloroform (1200ml) containing dibenzoyl peroxide (50 mg) under photoflood illumination. The reaction was complete after 2 hours, and the chloroform was removed under reduced pressure to give α-bromo-4-chloro-α-phenoxyacetophenone which was used without further purification. the chloroform was removed under reduced pressure

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Bromine (11.6g) in chloroform (40ml) was added dropwise to a stirred solution of 4-chloro-α-phenoxyacetophenone (18.8g) in chloroform (1200ml) containing dibenzoyl peroxide (50 mg) under photoflood illumination. The reaction was complete after 2 hours, and the chloroform was removed under reduced pressure to give α-bromo-4-chloro-α-phenoxyacetophenone which was used without further purification. the chloroform was removed under reduced pressure

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of 40.5 g (0.43 mole) of phenol, 100 g (0.428) of 4-chloro-α-bromoacetophenone, 100 g (0.725 mole) of potassium carbonate and 500 ml of glyme is heated to its reflux temperature and maintained at reflux for about 6 hours. The reaction mixture is evaporated to remove the solvent. The residue is diluted with water and diethyl ether and the layers are separated. The ether layer is washed with water and saturated sodium chloride solution and dried over magnesium sulfate. The ether solution is evaporated to provide a dark oil which gradually solidifies on cooling. The solid is recrystallized from ethanol to provide 4-chloro-α-phenoxyacetophenone, m.p. 81°-86° C. is heated to its reflux temperature maintained at reflux for about 6 hours The reaction mixture is evaporated to remove the solvent The residue is diluted with water and diethyl ether the layers are separated The ether layer is washed with water and saturated sodium chloride solution dried over magnesium sulfate The ether solution is evaporated to provide a dark oil which on cooling The solid is recrystallized from ethanol

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of 40.5 g. (0.43 mole) of phenol, 100 g. (0.428 mole) of 4-chloro-α-bromoacetophenone, 100 g. (0.725 mole) of potassium carbonate and 500 ml. of glyme is heated to its reflux temperature and maintained at reflux for about 6 hours. The reaction mixture is evaporated to remove the solvent. The residue is diluted with water and diethyl ether, and the layers are separated. The ether layer is washed with water and saturated sodium chloride solution and dried over magnesium sulfate. The ether solution is evaporated to provide a dark oil gradually solidifies on cooling. The solid is recrystallized from ethanol to provide 4-chloro-α-phenoxyacetophenone, m.p. 81°-86° C. A mixture of 40.5 g reflux temperature maintained at reflux for about 6 hours The reaction mixture is evaporated to remove the solvent The residue is diluted with water and diethyl ether the layers are separated The ether layer is washed with water and saturated sodium chloride solution dried over magnesium sulfate The ether solution is evaporated to provide a dark oil on cooling The solid is recrystallized from ethanol

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of 40.5 g (0.43 mole) of phenol, 100 g (0.428) of 4-chloro-α-bromoacetophenone, 100 g (0.725 mole) of potassium carbonate and 500 ml of glyme is heated to its reflux temperature and maintained at reflux for about 6 hours. The reaction mixture is evaporated to remove the solvent. The residue is diluted with water and diethyl ether and the layers are separated. The ether layer is washed with water and saturated sodium chloride solution and dried over magnesium sulfate. The ether solution is evaporated to provide a dark oil which gradually solidifies on cooling. The solid is recrystallized from ethanol to provide 4-chloro-α-phenoxyacetophenone, m.p. 81°-86° C. is heated to its reflux temperature maintained at reflux for about 6 hours The reaction mixture is evaporated to remove the solvent The residue is diluted with water and diethyl ether the layers are separated The ether layer is washed with water and saturated sodium chloride solution dried over magnesium sulfate The ether solution is evaporated to provide a dark oil which on cooling The solid is recrystallized from ethanol

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of 40.5 g. (0.43 mole) of phenol, 100 g. (0.428 mole) of 4-chloro-α-bromoacetophenone, 100 g. (0.725 mole) of potassium carbonate and 500 ml. of glyme is heated to its reflux temperature and maintained at reflux for about 6 hours. The reaction mixture is evaporated to remove the solvent. The residue is diluted with water and diethyl ether, and the layers are separated. The ether layer is washed with water and saturated sodium chloride solution and dried over magnesium sulfate. The ether solution is evaporated to provide a dark oil which gradually solidifies on cooling. The solid is recrystallized from ethanol to provide 4-chloro-α-phenoxyacetophenone, m.p. 81°-86° C. A mixture of 40.5 g reflux temperature maintained at reflux for about 6 hours The reaction mixture is evaporated to remove the solvent The residue is diluted with water and diethyl ether the layers are separated The ether layer is washed with water and saturated sodium chloride solution dried over magnesium sulfate The ether solution is evaporated to provide a dark oil which on cooling The solid is recrystallized from ethanol

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: By a procedure similar to that of example 1.85.3, starting from 2-(4-chlorophenoxy)-1-phenylethanone, (Z)-ethyl 4-(4-chlorophenoxy)-3-phenylbut-2-enoate and (E)-ethyl 4-(4-chlorophenoxy)-3-phenylbut-2-enoate were obtained as colourless oils.

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of 4-chlorophenol (0.774 g) and phenacyl bromide (1 g) in N,N-dimethyl formamide (10 ml) potassium carbonate (3.5 g) was added. The mixture was refluxed with stirring for 2 h. After cooling the reaction mixture was poured into water (50 ml) and extracted with dichloromethane (3×20 ml). The combined organic layers were washed with water (20 ml) and brine (20 ml), dried (MgSO4), and evaporated. The crude was purified by flash chromatography on silica gel (petrol ether/ethyl acetate 10:1) to give 2-(4-chlorophenoxy)-1-phenylethanone (1.22 g) as pale yellow solid. The mixture was refluxed After cooling the reaction mixture extracted with dichloromethane (3×20 ml) The combined organic layers were washed with water (20 ml) and brine (20 ml) dried (MgSO4) evaporated The crude was purified by flash chromatography on silica gel (petrol ether/ethyl acetate 10:1)

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Bromine (11.6g) in chloroform (40ml) was added dropwise to a stirred solution of 4-chloro-α-phenoxyacetophenone (18.8g) in chloroform (1200ml) containing dibenzoyl peroxide (50 mg) under photoflood illumination. The reaction was complete after 2 hours, and the chloroform was removed under reduced pressure to give α-bromo-4-chloro-α-phenoxyacetophenone which was used without further purification. the chloroform was removed under reduced pressure