(3-bromophenyl)methyl acetate

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Into a solution of 321 g. of 3-bromo benzaldehyde, 220 cm3 of 30% formaldehyde and 600 cm3. of methanol one-third of the solution of 300 g. of potassium hydroxide in 300 cm3. of water are dropped at 50° C. while stirring then the reaction mixture is stirred at this temperature for 1 hour. The temperature is raised to 60° C. and at this temperature the second third part of the base solution are dropped into the reaction mixture. After stirring the reaction mixture 1 hour at 60° C. the temperature is rised to 70° C. and at this temperature the last part of the base solution is dropped into the reaction mixture. The reaction mixture is stirred 1 hour at 70° C. then cooled to ambient temperature. The pH-value of the reaction mixture is adjusted with concentrated hydrochloric acid solution between 7.5 to 8 while maintaining the temperature at 40° C. From this reaction mixture 500 cm3. of methanol is distilled off, 500 cm3. of water are added to the residue then extracted twice with 150 cm3 of 1,2-dichloro ethane. From the united organic phase the water is removed by azeotropic distillation then 200 cm3. of acetic acid anhydride are dropped into the dichloro ethane solution while boiling and stirring. After boiling for 6 hours the reaction mixture is cooled, washed with 500 cm3. of water and 500 cm3. of 10% sodium hydrogen carbonate solution then evaporated. The residue is distilled in vacuo. 287.2 g. of 3-bromobenzyl acetate are obtained. Boiling point 123°-125° C./1200 Pa, nD24 : 1.5406, yield 72%. the reaction mixture is stirred at this temperature for 1 hour are dropped into the reaction mixture After stirring the reaction mixture 1 hour at 60° C. the temperature is rised to 70° C. and at this temperature is dropped into the reaction mixture The reaction mixture is stirred 1 hour at 70° C. then cooled to ambient temperature while maintaining the temperature at 40° C of methanol is distilled off of water are added to the residue then extracted twice with 150 cm3 of 1,2-dichloro ethane From the united organic phase the water is removed by azeotropic distillation of acetic acid anhydride are dropped into the dichloro ethane solution stirring the reaction mixture is cooled washed with 500 cm3 of 10% sodium hydrogen carbonate solution then evaporated The residue is distilled in vacuo

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Into a solution of 321 g. of 3-bromo benzaldehyde, 220 cm3 of 30% formaldehyde and 600 cm3. of methanol one-third of the solution of 300 g. of potassium hydroxide in 300 cm3. of water are dropped at 50° C. while stirring then the reaction mixture is stirred at this temperature for 1 hour. The temperature is raised to 60° C. and at this temperature the second third part of the base solution are dropped into the reaction mixture. After stirring the reaction mixture 1 hour at 60° C. the temperature is rised to 70° C. and at this temperature the last part of the base solution is dropped into the reaction mixture. The reaction mixture is stirred 1 hour at 70° C. then cooled to ambient temperature. The pH-value of the reaction mixture is adjusted with concentrated hydrochloric acid solution between 7.5 to 8 while maintaining the temperature at 40° C. From this reaction mixture 500 cm3. of methanol is distilled off, 500 cm3. of water are added to the residue then extracted twice with 150 cm3 of 1,2-dichloro ethane. From the united organic phase the water is removed by azeotropic distillation then 200 cm3. of acetic acid anhydride are dropped into the dichloro ethane solution while boiling and stirring. After boiling for 6 hours the reaction mixture is cooled, washed with 500 cm3. of water and 500 cm3. of 10% sodium hydrogen carbonate solution then evaporated. The residue is distilled in vacuo. 287.2 g. of 3-bromobenzyl acetate are obtained. Boiling point 123°-125° C./1200 Pa, nD24 : 1.5406, yield 72%. the reaction mixture is stirred at this temperature for 1 hour are dropped into the reaction mixture After stirring the reaction mixture 1 hour at 60° C. the temperature is rised to 70° C. and at this temperature is dropped into the reaction mixture The reaction mixture is stirred 1 hour at 70° C. then cooled to ambient temperature while maintaining the temperature at 40° C of methanol is distilled off of water are added to the residue then extracted twice with 150 cm3 of 1,2-dichloro ethane From the united organic phase the water is removed by azeotropic distillation of acetic acid anhydride are dropped into the dichloro ethane solution stirring the reaction mixture is cooled washed with 500 cm3 of 10% sodium hydrogen carbonate solution then evaporated The residue is distilled in vacuo

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

Procedure: 28.29 g. (0.3 mole) of phenol, 11.2 g. (0.2 mole) of potassium hydroxide and 20 cm3. of xylene are weighed together. The water is azeotropically distilled with stirring and boiling then the xylene is also distilled. To the reaction mixture 1.0 g. of copper(I) chloride and 1.0 g. of activated copper are added and in oil bath of 180° C. 22.91 g. (0.1 mole) 3-bromobenzyl acetate are dropped during 25 minutes while stirring. The reaction mixture is stirred at the same temperature for an additional two hours. After cooling 50 cm3. of 15% sodium chloride solution are added to the reaction mixture, then the reaction mixture is filtered off. The filtrate is extracted twice with 30 cm3 of toluene. The united organic phase is washed with a mixture of 30 cm3. of 15% sodium chloride solution and 10 cm3. of 40% sodium hydroxide solution. The organic phase is evaporated and the residue distilled in vacuo. 17.2 g. of 3-phenoxybenzyl acetate are obtained. Boiling point 142°-145° C./53.2 Pa, nD20 : 1.5621, yield 71%. The water is azeotropically distilled the xylene is also distilled of activated copper are added and in oil bath of 180° C while stirring The reaction mixture is stirred at the same temperature for an additional two hours After cooling 50 cm3 the reaction mixture is filtered off The filtrate is extracted twice with 30 cm3 of toluene The united organic phase is washed with a mixture of 30 cm3 The organic phase is evaporated the residue distilled in vacuo

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

Procedure: 28.29 g. (0.3 mole) of phenol, 11.2 g. (0.2 mole) of potassium hydroxide and 20 cm3. of xylene are weighed together. The water is azeotropically distilled with stirring and boiling then the xylene is also distilled. To the reaction mixture 1.0 g. of copper(I) chloride and 1.0 g. of activated copper are added and in oil bath of 180° C. 22.91 g. (0.1 mole) 3-bromobenzyl acetate are dropped during 25 minutes while stirring. The reaction mixture is stirred at the same temperature for an additional two hours. After cooling 50 cm3. of 15% sodium chloride solution are added to the reaction mixture, then the reaction mixture is filtered off. The filtrate is extracted twice with 30 cm3 of toluene. The united organic phase is washed with a mixture of 30 cm3. of 15% sodium chloride solution and 10 cm3. of 40% sodium hydroxide solution. The organic phase is evaporated and the residue distilled in vacuo. 17.2 g. of 3-phenoxybenzyl acetate are obtained. Boiling point 142°-145° C./53.2 Pa, nD20 : 1.5621, yield 71%. The water is azeotropically distilled the xylene is also distilled of activated copper are added and in oil bath of 180° C while stirring The reaction mixture is stirred at the same temperature for an additional two hours After cooling 50 cm3 the reaction mixture is filtered off The filtrate is extracted twice with 30 cm3 of toluene The united organic phase is washed with a mixture of 30 cm3 The organic phase is evaporated the residue distilled in vacuo

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

Procedure: 10.35 g. (0.11 mole) of phenol, 6.15 g. (0.11 mole) of potassium hydroxide and 35 cm3. of xylene are weighed together. The water is azeotropically distilled with stirring and boiling. 5 cm3. of pyridine and 0.5 g. of copper(I) chloride are added then 22.91 g. (0.1 mole) of 3-bromobenzyl acetate are dropped into the reaction mixture during 15 minutes with stirring and boiling. The reaction mixture is boiled with stirring for an additional three hours. After cooling the reaction mixture is filtered off and the filtrate washed with a mixture of 25 cm3. of 15% sodium chloride solution and 2 cm3. of 40% sodium hydroxide solution. The organic phase is evaporated in vacuo. The residue is distilled in vacuo and so 18.65 g. of 3-phenoxybenzyl acetate are obtained. Boiling point 142°-145° C./53.2 Pa, nD20 : 1.5621, yield 77%. The water is azeotropically distilled of copper(I) chloride are added with stirring with stirring for an additional three hours After cooling the reaction mixture is filtered off the filtrate washed with a mixture of 25 cm3 The organic phase is evaporated in vacuo The residue is distilled in vacuo and so 18.65 g

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

Procedure: 10.35 g. (0.11 mole) of phenol, 6.15 g. (0.11 mole) of potassium hydroxide and 35 cm3. of xylene are weighed together. The water is azeotropically distilled with stirring and boiling. 5 cm3. of pyridine and 0.5 g. of copper(I) chloride are added then 22.91 g. (0.1 mole) of 3-bromobenzyl acetate are dropped into the reaction mixture during 15 minutes with stirring and boiling. The reaction mixture is boiled with stirring for an additional three hours. After cooling the reaction mixture is filtered off and the filtrate washed with a mixture of 25 cm3. of 15% sodium chloride solution and 2 cm3. of 40% sodium hydroxide solution. The organic phase is evaporated in vacuo. The residue is distilled in vacuo and so 18.65 g. of 3-phenoxybenzyl acetate are obtained. Boiling point 142°-145° C./53.2 Pa, nD20 : 1.5621, yield 77%. The water is azeotropically distilled of copper(I) chloride are added with stirring with stirring for an additional three hours After cooling the reaction mixture is filtered off the filtrate washed with a mixture of 25 cm3 The organic phase is evaporated in vacuo The residue is distilled in vacuo and so 18.65 g

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Into a solution of 321 g. of 3-bromo benzaldehyde, 220 cm3 of 30% formaldehyde and 600 cm3. of methanol one-third of the solution of 300 g. of potassium hydroxide in 300 cm3. of water are dropped at 50° C. while stirring then the reaction mixture is stirred at this temperature for 1 hour. The temperature is raised to 60° C. and at this temperature the second third part of the base solution are dropped into the reaction mixture. After stirring the reaction mixture 1 hour at 60° C. the temperature is rised to 70° C. and at this temperature the last part of the base solution is dropped into the reaction mixture. The reaction mixture is stirred 1 hour at 70° C. then cooled to ambient temperature. The pH-value of the reaction mixture is adjusted with concentrated hydrochloric acid solution between 7.5 to 8 while maintaining the temperature at 40° C. From this reaction mixture 500 cm3. of methanol is distilled off, 500 cm3. of water are added to the residue then extracted twice with 150 cm3 of 1,2-dichloro ethane. From the united organic phase the water is removed by azeotropic distillation then 200 cm3. of acetic acid anhydride are dropped into the dichloro ethane solution while boiling and stirring. After boiling for 6 hours the reaction mixture is cooled, washed with 500 cm3. of water and 500 cm3. of 10% sodium hydrogen carbonate solution then evaporated. The residue is distilled in vacuo. 287.2 g. of 3-bromobenzyl acetate are obtained. Boiling point 123°-125° C./1200 Pa, nD24 : 1.5406, yield 72%. the reaction mixture is stirred at this temperature for 1 hour are dropped into the reaction mixture After stirring the reaction mixture 1 hour at 60° C. the temperature is rised to 70° C. and at this temperature is dropped into the reaction mixture The reaction mixture is stirred 1 hour at 70° C. then cooled to ambient temperature while maintaining the temperature at 40° C of methanol is distilled off of water are added to the residue then extracted twice with 150 cm3 of 1,2-dichloro ethane From the united organic phase the water is removed by azeotropic distillation of acetic acid anhydride are dropped into the dichloro ethane solution stirring the reaction mixture is cooled washed with 500 cm3 of 10% sodium hydrogen carbonate solution then evaporated The residue is distilled in vacuo

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

Procedure: 28.29 g. (0.3 mole) of phenol, 11.2 g. (0.2 mole) of potassium hydroxide and 20 cm3. of xylene are weighed together. The water is azeotropically distilled with stirring and boiling then the xylene is also distilled. To the reaction mixture 1.0 g. of copper(I) chloride and 1.0 g. of activated copper are added and in oil bath of 180° C. 22.91 g. (0.1 mole) 3-bromobenzyl acetate are dropped during 25 minutes while stirring. The reaction mixture is stirred at the same temperature for an additional two hours. After cooling 50 cm3. of 15% sodium chloride solution are added to the reaction mixture, then the reaction mixture is filtered off. The filtrate is extracted twice with 30 cm3 of toluene. The united organic phase is washed with a mixture of 30 cm3. of 15% sodium chloride solution and 10 cm3. of 40% sodium hydroxide solution. The organic phase is evaporated and the residue distilled in vacuo. 17.2 g. of 3-phenoxybenzyl acetate are obtained. Boiling point 142°-145° C./53.2 Pa, nD20 : 1.5621, yield 71%. The water is azeotropically distilled the xylene is also distilled of activated copper are added and in oil bath of 180° C while stirring The reaction mixture is stirred at the same temperature for an additional two hours After cooling 50 cm3 the reaction mixture is filtered off The filtrate is extracted twice with 30 cm3 of toluene The united organic phase is washed with a mixture of 30 cm3 The organic phase is evaporated the residue distilled in vacuo

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

Procedure: 10.35 g. (0.11 mole) of phenol, 6.15 g. (0.11 mole) of potassium hydroxide and 35 cm3. of xylene are weighed together. The water is azeotropically distilled with stirring and boiling. 5 cm3. of pyridine and 0.5 g. of copper(I) chloride are added then 22.91 g. (0.1 mole) of 3-bromobenzyl acetate are dropped into the reaction mixture during 15 minutes with stirring and boiling. The reaction mixture is boiled with stirring for an additional three hours. After cooling the reaction mixture is filtered off and the filtrate washed with a mixture of 25 cm3. of 15% sodium chloride solution and 2 cm3. of 40% sodium hydroxide solution. The organic phase is evaporated in vacuo. The residue is distilled in vacuo and so 18.65 g. of 3-phenoxybenzyl acetate are obtained. Boiling point 142°-145° C./53.2 Pa, nD20 : 1.5621, yield 77%. The water is azeotropically distilled of copper(I) chloride are added with stirring with stirring for an additional three hours After cooling the reaction mixture is filtered off the filtrate washed with a mixture of 25 cm3 The organic phase is evaporated in vacuo The residue is distilled in vacuo and so 18.65 g

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Into a solution of 321 g. of 3-bromo benzaldehyde, 220 cm3 of 30% formaldehyde and 600 cm3. of methanol one-third of the solution of 300 g. of potassium hydroxide in 300 cm3. of water are dropped at 50° C. while stirring then the reaction mixture is stirred at this temperature for 1 hour. The temperature is raised to 60° C. and at this temperature the second third part of the base solution are dropped into the reaction mixture. After stirring the reaction mixture 1 hour at 60° C. the temperature is rised to 70° C. and at this temperature the last part of the base solution is dropped into the reaction mixture. The reaction mixture is stirred 1 hour at 70° C. then cooled to ambient temperature. The pH-value of the reaction mixture is adjusted with concentrated hydrochloric acid solution between 7.5 to 8 while maintaining the temperature at 40° C. From this reaction mixture 500 cm3. of methanol is distilled off, 500 cm3. of water are added to the residue then extracted twice with 150 cm3 of 1,2-dichloro ethane. From the united organic phase the water is removed by azeotropic distillation then 200 cm3. of acetic acid anhydride are dropped into the dichloro ethane solution while boiling and stirring. After boiling for 6 hours the reaction mixture is cooled, washed with 500 cm3. of water and 500 cm3. of 10% sodium hydrogen carbonate solution then evaporated. The residue is distilled in vacuo. 287.2 g. of 3-bromobenzyl acetate are obtained. Boiling point 123°-125° C./1200 Pa, nD24 : 1.5406, yield 72%. the reaction mixture is stirred at this temperature for 1 hour are dropped into the reaction mixture After stirring the reaction mixture 1 hour at 60° C. the temperature is rised to 70° C. and at this temperature is dropped into the reaction mixture The reaction mixture is stirred 1 hour at 70° C. then cooled to ambient temperature while maintaining the temperature at 40° C of methanol is distilled off of water are added to the residue then extracted twice with 150 cm3 of 1,2-dichloro ethane From the united organic phase the water is removed by azeotropic distillation of acetic acid anhydride are dropped into the dichloro ethane solution stirring the reaction mixture is cooled washed with 500 cm3 of 10% sodium hydrogen carbonate solution then evaporated The residue is distilled in vacuo

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

Procedure: 28.29 g. (0.3 mole) of phenol, 11.2 g. (0.2 mole) of potassium hydroxide and 20 cm3. of xylene are weighed together. The water is azeotropically distilled with stirring and boiling then the xylene is also distilled. To the reaction mixture 1.0 g. of copper(I) chloride and 1.0 g. of activated copper are added and in oil bath of 180° C. 22.91 g. (0.1 mole) 3-bromobenzyl acetate are dropped during 25 minutes while stirring. The reaction mixture is stirred at the same temperature for an additional two hours. After cooling 50 cm3. of 15% sodium chloride solution are added to the reaction mixture, then the reaction mixture is filtered off. The filtrate is extracted twice with 30 cm3 of toluene. The united organic phase is washed with a mixture of 30 cm3. of 15% sodium chloride solution and 10 cm3. of 40% sodium hydroxide solution. The organic phase is evaporated and the residue distilled in vacuo. 17.2 g. of 3-phenoxybenzyl acetate are obtained. Boiling point 142°-145° C./53.2 Pa, nD20 : 1.5621, yield 71%. The water is azeotropically distilled the xylene is also distilled of activated copper are added and in oil bath of 180° C while stirring The reaction mixture is stirred at the same temperature for an additional two hours After cooling 50 cm3 the reaction mixture is filtered off The filtrate is extracted twice with 30 cm3 of toluene The united organic phase is washed with a mixture of 30 cm3 The organic phase is evaporated the residue distilled in vacuo

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

Procedure: 10.35 g. (0.11 mole) of phenol, 6.15 g. (0.11 mole) of potassium hydroxide and 35 cm3. of xylene are weighed together. The water is azeotropically distilled with stirring and boiling. 5 cm3. of pyridine and 0.5 g. of copper(I) chloride are added then 22.91 g. (0.1 mole) of 3-bromobenzyl acetate are dropped into the reaction mixture during 15 minutes with stirring and boiling. The reaction mixture is boiled with stirring for an additional three hours. After cooling the reaction mixture is filtered off and the filtrate washed with a mixture of 25 cm3. of 15% sodium chloride solution and 2 cm3. of 40% sodium hydroxide solution. The organic phase is evaporated in vacuo. The residue is distilled in vacuo and so 18.65 g. of 3-phenoxybenzyl acetate are obtained. Boiling point 142°-145° C./53.2 Pa, nD20 : 1.5621, yield 77%. The water is azeotropically distilled of copper(I) chloride are added with stirring with stirring for an additional three hours After cooling the reaction mixture is filtered off the filtrate washed with a mixture of 25 cm3 The organic phase is evaporated in vacuo The residue is distilled in vacuo and so 18.65 g