2 4 6-TRICHLOROBENZYL ALCOHOL 97

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

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 solution of 2,4,6-trichlorobenzylalcohol (10.0 g; 47.3 mmol) in chloroform (100 ml) kept under nitrogen atmosphere, thionyl chloride (6.07 ml; 85.1 mmol) was added slowly at 0° C. over a period of 15 minutes followed by catalytic amount of DMF. The reaction mix was allowed to stir at ambient temp for 3 hours. The reaction mixture was quenched with 50 ml of water; the aqueous layer was extracted with DCM (3×100 ml). The combined organic layer was washed with 5% sodium bicarbonate solution (2×50 ml) followed by brine (50 ml) and dried over anhydrous sodium sulphate. The solvent was evaporated under reduced pressure. 10.9 g (100% of theory) of 1,3,5-trichloro-2-chloromethyl-benzene was obtained in form of a white solid. The reaction mix The reaction mixture was quenched with 50 ml of water the aqueous layer was extracted with DCM (3×100 ml) The combined organic layer was washed with 5% sodium bicarbonate solution (2×50 ml) dried over anhydrous sodium sulphate The solvent was evaporated under reduced pressure

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

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 solution of 2,4,6-trichlorobenzylalcohol (10.0 g; 47.3 mmoles) in chloroform (100 ml) kept under nitrogen atmosphere, thionyl chloride (6.07 mL, 85.1 mmole) was added slowly at 0° C. over a period of 15 minutes followed by catalytic amount of DMF. The reaction mix was allowed to stir at ambient temp for 3 hours. The reaction mixture was quenched with 50 mL of water; the aqueous layer was extracted with DCM (3×100 ml). The combined organic layer was washed with 5% sodium bicarbonate solution (2×50 ml) followed by brine (50 ml) and dried over anhydrous sodium sulphate. The solvent was evaporated under reduced pressure. 10.9 g (100.0% of theory) of 1,3,5-trichloro-2-chloromethyl-benzene was obtained in form of a white solid. The reaction mix The reaction mixture was quenched with 50 mL of water the aqueous layer was extracted with DCM (3×100 ml) The combined organic layer was washed with 5% sodium bicarbonate solution (2×50 ml) dried over anhydrous sodium sulphate The solvent was evaporated under reduced pressure

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

実験手順: A solution of lithium aluminium hydride (1M in THF, 18 mmol, 18 ml) was added slowly to a solution of 2,4,6-trichlorobenzoyl chloride (4.35 g, 17.8 mmol) in THF (70 ml) at 0°. After 1 h water (685 μl) was added, followed by aqueous sodium hydroxide (3M, 685 μl) and more water (2.06 ml). The suspension was stirred vigorously for 1 h, the precipitate filtered off and the filtrate evaporated in vacuo to give a slightly yellow solid. Recrystallisation from diisopropylether gave the title compound as white needles (2.63 g, 70%), m.p. 100-101°δH (CDCl3) 7.35 (2H, s, ArH), 4.91 (2H, br s, CH2CH) and 2.07 (1H, br s, CH); m/z (ES, 60V) 193 (M--OH). the precipitate filtered off the filtrate evaporated in vacuo to give a slightly yellow solid Recrystallisation from diisopropylether

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

実験手順: A solution of lithium aluminium hydride (1M in THF, 18 mmol, 18 ml) was added slowly to a solution of 2,4,6-trichlorobenzoyl chloride (4.35 g, 17.8 mmol) in THF (70 ml) at 0°. After 1 h water (685 μl) was added, followed by aqueous sodium hydroxide (3M, 685 μl) and more water (2.06 ml). The suspension was stirred vigorously for 1 h, the precipitate filtered off and the filtrate evaporated in vacuo to give a slightly yellow solid. Recrystallisation from diisopropylether gave the title compound as white needles (2.63 g, 70%), m.p. 100-101°δH (CDCl3) 7.35 (2H, s, ArH), 4.91 (2H, br s, CH2CH) and 2.07 (1H, br s, CH); m/z (ES, 60V) 193 (M--OH). the precipitate filtered off the filtrate evaporated in vacuo to give a slightly yellow solid Recrystallisation from diisopropylether

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

実験手順: A solution of lithium aluminium hydride (1M in THF, 18 mmol, 18 ml) was added slowly to a solution of 2,4,6-trichlorobenzoyl chloride (4.35 g, 17.8 mmol) in THF (70 ml) at 0°. After 1 h water (685 μl) was added, followed by aqueous sodium hydroxide (3M, 685 μl) and more water (2.06 ml). The suspension was stirred vigorously for 1 h, the precipitate filtered off and the filtrate evaporated in vacuo to give a slightly yellow solid. Recrystallisation from diisopropylether gave the title compound as white needles (2.63 g, 70%), m.p. 100-101°δH (CDCl3) 7.35 (2H, s, ArH), 4.91 (2H, br s, CH2CH) and 2.07 (1H, br s, CH); m/z (ES, 60V) 193 (M--OH). the precipitate filtered off the filtrate evaporated in vacuo to give a slightly yellow solid Recrystallisation from diisopropylether

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

実験手順: A solution of lithium aluminium hydride (1M in THF, 18 ml, 18 mmol) was added to a solution of 2,4,6-trichlorobenzoyl chloride (4.35 g, 17.8 mmol ) in THF (70 ml) at 0°. After 1 h, water (685 μl), aqueous NaOH (3M, 685 μl) and water (2.06 ml) were added. The mixture was stirred vigorously for 1 h, the precipitate filtered off and the filtrate evaporated in vacuo to give a yellow solid. Recrystallisation from diisopropylether gave the title compound as white needles (2.63 g, 70%), m.p. 100-101°. δH (CDCl3) 7.35 (2 H, s, ArH), 4.91 (2 H, br s, CH2OH), 2.07 (1 H, br s, CH2OH). the precipitate filtered off the filtrate evaporated in vacuo to give a yellow solid Recrystallisation from diisopropylether