2-(2,4-dichlorophenoxy)propan-1-ol

反応条件: temp:0.00; pressure:0.00; stir:

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

実験手順: To a stirred mixture of 324 parts of 2-(2,4-dichlorophenoxy)-1-propanol and 700 parts of N,N-diethylethanamine were added dropwise at room temperature 335 parts of methanesulfonyl chloride (exothermic reaction: the temperature roses to reflux temperature). While cooling in a water-bath, stirring was continued for 30 minutes at room temperature. The reaction mixture was poured onto water and the product was extracted with 2,2'-oxybispropane. The extract was dried, filtered and evaporated. The residue was distilled by vacuum distillation, yielding 300 parts of 2-(2,4-dichlorophenoxy)-1-propanol methanesulfonate (ester); bp. 130° C. at 2×10-4 mm. pressure (intermediate 101). exothermic reaction the temperature roses to reflux temperature) While cooling in a water-bath The reaction mixture was poured onto water the product was extracted with 2,2'-oxybispropane The extract was dried filtered evaporated The residue was distilled by vacuum distillation

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

実験手順: To a stirred mixture of 324 parts of 2-(2,4-dichloro-phenoxy)-1-propanol and 700 parts of N,N-diethylethanamine were added dropwise at room temperature 335 parts of methanesulfonyl chloride (exothermic reaction: the temperature roses to reflux temperature). While cooling in a water-bath, stirring was continued for 30 minutes at room temperature. The reaction mixture was poured onto water and the product was extracted with 2,2'-oxybispropane. The extract was dried, filtered and evaporated. The residue was distilled by vacuum distillation, yielding 300 parts of 2-(2,4-dichlorophenoxy)-1-propanol methanesulfonate (ester); bp. 130° C. at 2×10-4 mm. pressure (intermediate 101). exothermic reaction the temperature roses to reflux temperature) While cooling in a water-bath The reaction mixture was poured onto water the product was extracted with 2,2'-oxybispropane The extract was dried filtered evaporated The residue was distilled by vacuum distillation

反応条件: temp:-60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 4.68 g of DMSO were added under nitrogen to a stirred solution of 3.81 g of oxalyl chloride in 75 ml of methylene chloride at -60° C. to -50° C. After 2 minutes a solution of 6.4 g of 2-(2,4-dichlorophenoxy)propanol in 40 ml of methylene chloride was added. The mixture was stirred at -60° C. for a further 15 minutes and was then treated with 13.7 g of triethylamine After a further 5 minutes at -60° C. the mixture was allowed to warm to room temperature. 150 ml of water were added and the layers were separated. The aqueous layer was extracted with 150 ml of methylene chloride and the combined organic extracts were washed successively with sodium chloride solution, dilute hydrochloric acid, water, dilute sodium carbonate solution and water, dried over sodium sulphate and evaporated. The residue was purified by chromatography on silica gel using ethyl acetate/n-hexane (1:4) for the elution. There were obtained 1.4 g of 2-(2,4-dichlorophenoxy)propionaldehyde, mp 87°-88° C. to warm to room temperature the layers were separated The aqueous layer was extracted with 150 ml of methylene chloride the combined organic extracts were washed successively with sodium chloride solution, dilute hydrochloric acid, water, dilute sodium carbonate solution and water dried over sodium sulphate evaporated The residue was purified by chromatography on silica gel for the elution

反応条件: temp:-60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 4.68 g of DMSO were added under nitrogen to a stirred solution of 3.81 g of oxalyl chloride in 75 ml of methylene chloride at -60° C. to -50° C. After 2 minutes a solution of 6.4 g of 2-(2,4-dichlorophenoxy)propanol in 40 ml of methylene chloride was added. The mixture was stirred at -60° C. for a further 15 minutes and was then treated with 13.7 g of triethylamine After a further 5 minutes at -60° C. the mixture was allowed to warm to room temperature. 150 ml of water were added and the layers were separated. The aqueous layer was extracted with 150 ml of methylene chloride and the combined organic extracts were washed successively with sodium chloride solution, dilute hydrochloric acid, water, dilute sodium carbonate solution and water, dried over sodium sulphate and evaporated. The residue was purified by chromatography on silica gel using ethyl acetate/n-hexane (1:4) for the elution. There were obtained 1.4 g of 2-(2,4-dichlorophenoxy)propionaldehyde, mp 87°-88° C. to warm to room temperature the layers were separated The aqueous layer was extracted with 150 ml of methylene chloride the combined organic extracts were washed successively with sodium chloride solution, dilute hydrochloric acid, water, dilute sodium carbonate solution and water dried over sodium sulphate evaporated The residue was purified by chromatography on silica gel for the elution

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

実験手順: 43 ml of a 1 M solution of borane in tetrahydrofuran (THF) were stirred under nitrogen and cooled in ice while a solution of 6.8 g of 2-(2,4-dichlorophenoxy)propionic acid in 40 ml of THF was added dropwise thereto. The mixture was heated to boiling under reflux for 1 hour and then cooled to room temperature. 22 ml of a saturated solution of hydrogen chloride in methanol were added dropwise and the solution was heated to boiling under reflux for 1 hour. The mixture was evaporated and the residue was treated with 22 ml of a saturated solution of hydrogen chloride in methanol. After heating under reflux for 1 hour the mixture was evaporated and the residue was partitioned between 100 ml of saturated sodium bicarbonate solution and 100 ml of methylene chloride. The layers were separated and the aqueous layer was extracted with 100 ml of methylene chloride. The combined organic extracts were dried over sodium sulphate and evaporated to give 6.4 g of 2-(2,4-dichlorophenoxy)-propanol as a yellow oil. was added dropwise The mixture was heated under reflux for 1 hour the solution was heated under reflux for 1 hour The mixture was evaporated the residue was treated with 22 ml of a saturated solution of hydrogen chloride in methanol After heating under reflux for 1 hour the mixture was evaporated the residue was partitioned between 100 ml of saturated sodium bicarbonate solution and 100 ml of methylene chloride The layers were separated the aqueous layer was extracted with 100 ml of methylene chloride The combined organic extracts were dried over sodium sulphate evaporated

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

実験手順: To a stirred mixture of 324 parts of 2-(2,4-dichlorophenoxy)-1-propanol and 700 parts of N,N-diethylethanamine were added dropwise at room temperature 335 parts of methanesulfonyl chloride (exothermic reaction: the temperature roses to reflux temperature). While cooling in a water-bath, stirring was continued for 30 minutes at room temperature. The reaction mixture was poured onto water and the product was extracted with 2,2'-oxybispropane. The extract was dried, filtered and evaporated. The residue was distilled by vacuum distillation, yielding 300 parts of 2-(2,4-dichlorophenoxy)-1-propanol methanesulfonate (ester); bp. 130° C. at 2×10-4 mm. pressure (intermediate 101). exothermic reaction the temperature roses to reflux temperature) While cooling in a water-bath The reaction mixture was poured onto water the product was extracted with 2,2'-oxybispropane The extract was dried filtered evaporated The residue was distilled by vacuum distillation

反応条件: temp:-60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 4.68 g of DMSO were added under nitrogen to a stirred solution of 3.81 g of oxalyl chloride in 75 ml of methylene chloride at -60° C. to -50° C. After 2 minutes a solution of 6.4 g of 2-(2,4-dichlorophenoxy)propanol in 40 ml of methylene chloride was added. The mixture was stirred at -60° C. for a further 15 minutes and was then treated with 13.7 g of triethylamine. After a further 5 minutes at -60° C. the mixture was allowed to warm to room temperature. 150 ml of water were added and the layers were separated. The aqueous layer was extracted with 150 ml of methylene chloride and the combined organic extracts were washed successively with sodium chloride solution, dilute hydrochloric acid, water, dilute sodium carbonate solution and water, dried over sodium sulphate and evaporated. The residue was purified by chromatography on silica gel using ethyl acetate/n-hexane (1:4) for the elution. There were obtained 1.4 g of 2-(2,4-dichlorophenoxy)propionaldehyde, mp 87°-88° C. After a further 5 minutes at -60° C. the mixture was allowed to warm to room temperature the layers were separated The aqueous layer was extracted with 150 ml of methylene chloride the combined organic extracts were washed successively with sodium chloride solution, dilute hydrochloric acid, water, dilute sodium carbonate solution and water dried over sodium sulphate evaporated The residue was purified by chromatography on silica gel for the elution

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

実験手順: 43 ml of a 1M solution of borane in tetrahydrofuran (THF) were stirred under nitrogen and cooled in ice while a solution of 6.8 g of 2-(2,4-dichlorophenoxy)propionic acid in 40 ml of THF was added dropwise thereto. The mixture was heated to boiling under reflux for 1 hour and then cooled to room temperature. 22 ml of a saturated solution of hydrogen chloride in methanol were added dropwise and the solution was heated to boiling under reflux for 1 hour. The mixture was evaporated and the residue was treated with 22 ml of a saturated solution of hydrogen chloride in methanol. After heating under reflux for 1 hour the mixture was evaporated and the residue was partitioned between 100 ml of saturated sodium bicarbonate solution and 100 ml of methylene chloride. The layers were separated and the aqueous layer was extracted with 100 ml of methylene chloride. The combined organic extracts were dried over sodium sulphate and evaporated to gave 6.4 g of 2-(2,4-dichlorophenoxy)propanol as a yellow oil. was added dropwise The mixture was heated under reflux for 1 hour the solution was heated under reflux for 1 hour The mixture was evaporated the residue was treated with 22 ml of a saturated solution of hydrogen chloride in methanol After heating under reflux for 1 hour the mixture was evaporated the residue was partitioned between 100 ml of saturated sodium bicarbonate solution and 100 ml of methylene chloride The layers were separated the aqueous layer was extracted with 100 ml of methylene chloride The combined organic extracts were dried over sodium sulphate evaporated

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

実験手順: 43 ml of a 1M solution of borane in tetrahydrofuran (THF) were stirred under nitrogen and cooled in ice while a solution of 6.8 g of 2-(2,4-dichlorophenoxy)propionic acid in 40 ml of THF was added dropwise thereto. The mixture was heated to boiling under reflux for 1 hour and then cooled to room temperature. 22 ml of a saturated solution of hydrogen chloride in methanol were added dropwise and the solution was heated to boiling under reflux for 1 hour. The mixture was evaporated and the residue was treated with 22 ml of a saturated solution of hydrogen chloride in methanol. After heating under reflux for 1 hour the mixture was evaporated and the residue was partitioned between 100 ml of saturated sodium bicarbonate solution and 100 ml of methylene chloride. The layers were separated and the aqueous layer was extracted with 100 ml of methylene chloride. The combined organic extracts were dried over sodium sulphate and evaporated to gave 6.4 g of 2-(2,4-dichlorophenoxy)propanol as a yellow oil. was added dropwise The mixture was heated under reflux for 1 hour the solution was heated under reflux for 1 hour The mixture was evaporated the residue was treated with 22 ml of a saturated solution of hydrogen chloride in methanol After heating under reflux for 1 hour the mixture was evaporated the residue was partitioned between 100 ml of saturated sodium bicarbonate solution and 100 ml of methylene chloride The layers were separated the aqueous layer was extracted with 100 ml of methylene chloride The combined organic extracts were dried over sodium sulphate evaporated

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

実験手順: To a stirred mixture of 324 parts of 2-(2,4-dichlorophenoxy)-1-propanol and 700 parts of N,N-diethylethanamine were added dropwise at room temperature 335 parts of methanesulfonyl chloride (exothermic reaction: the temperature roses to reflux temperature). While cooling in a water-bath, stirring was continued for 30 minutes at room temperature. The reaction mixture was poured onto water and the product was extracted with 2,2'-oxybispropane. The extract was dried, filtered and evaporated. The residue was distilled by vacuum distillation, yielding 300 parts of 2-(2,4-dichlorophenoxy)-1-propanol methanesulfonate (ester); bp. 130° C. at 2×10-4 mm. pressure (intermediate 101). exothermic reaction the temperature roses to reflux temperature) While cooling in a water-bath The reaction mixture was poured onto water the product was extracted with 2,2'-oxybispropane The extract was dried filtered evaporated The residue was distilled by vacuum distillation

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

実験手順: To a stirred mixture of 324 parts of 2-(2,4-dichlorophenoxy)-1-propanol and 700 parts of N,N-diethylethanamine were added dropwise at room temperature 335 parts of methanesulfonyl chloride (exothermic reaction: the temperature roses to reflux temperature). While cooling in a water-bath, stirring was continued for 30 minutes at room temperature. The reaction mixture was poured onto water and the product was extracted with 2,2'-oxybispropane. The extract was dried, filtered and evaporated. The residue was distilled by vacuum distillation, yielding 300 parts of 2-(2,4-dichlorophenoxy)-1-propanol methanesulfonate (ester); bp. 130° C. at 2×10-4 mm. pressure (intermediate 101). exothermic reaction the temperature roses to reflux temperature) While cooling in a water-bath The reaction mixture was poured onto water the product was extracted with 2,2'-oxybispropane The extract was dried filtered evaporated The residue was distilled by vacuum distillation