2-(羟甲基)-4-甲氧基苯酚

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Under ice cooling, the solution of 5-methoxysalicylaldehyde (5 g) in ether (20 ml) was slowly added dropwise to the suspension of LiAlH4 (0.75 g) in ether (50 ml). After stirring at room temperature for 2 hours, another addition of LiAlH4 (0.5 g) was carried out under ice cooling, with subsequent stirring at room temperature for 30 minutes. To the reaction solution was added ice carefully, followed by sequential addition of 1N HCl and ether. After filtering off insoluble materials using Celite™, the ether layer was separated from the filtrate, and then, the aqueous phase was further extracted with ether. The combined ether layers were washed with saturated sodium chloride solution, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the residue was washed with ether-hexane and filtered to give the title compound (3.9 g; 77%). with subsequent stirring at room temperature for 30 minutes To the reaction solution was added ice carefully After filtering off insoluble materials the ether layer was separated from the filtrate the aqueous phase was further extracted with ether The combined ether layers were washed with saturated sodium chloride solution dried over anhydrous sodium sulfate The solvent was removed under reduced pressure the residue was washed with ether-hexane filtered

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: In the course of 30 minutes, at from 40° to 60°, 18 g of hydrogen chloride are introduced into a solution of 49.8 g of 2-hydroxy-5-methoxy-benzyl alcohol and 115.8 g of triphenylphosphane in 150 ml of acetonitrile. The reaction mixture is then stirred for 5 hours at 75°, the product beginning to crystallise after approx. 30 minutes. The reaction mixture is cooled to 0°, stirred for a further one hour and then at that temperature the crystals are filtered off with suction. [(2-Hydroxy-5-methoxy-phenyl)methyl]-triphenyl-phosphonium chloride is thus obtained in the form of colourless crystals [m.p.: 270° (decomposition); IR (KBr): 2990, 1585, 1395, 1295, 1240, 1145, 995 cm-1 ; 1H-NMR (360 MHz, CH3OH-d4 : 3.47 (s, 3H, OCH3), 4.74 (d, 2H, CH2P+), 6.40 (dd, 1H), 6.62 (d, 1H), 6.73 (m, 1H), 7.56 to 7.72 (m, 12H), 7.87 (m, 3H) ppm]; yield 78% of the theoretical yield. to crystallise after approx. 30 minutes The reaction mixture is cooled to 0° stirred for a further one hour at that temperature the crystals are filtered off with suction

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: In the course of 30 minutes, at from 40° to 60°, 18 g of hydrogen chloride are introduced into a solution of 49.8 g of 2-hydroxy-5-methoxy-benzyl alcohol and 115.8 g of triphenylphosphane in 150 ml of acetonitrile. The reaction mixture is then stirred for 5 hours at 75°, the product beginning to crystallise after approx. 30 minutes. The reaction mixture is cooled to 0°, stirred for a further one hour and then at that temperature the crystals are filtered off with suction. [(2-Hydroxy-5-methoxy-phenyl)methyl]-triphenyl-phosphonium chloride is thus obtained in the form of colourless crystals [m.p.: 270° (decomposition); IR (KBr): 2990, 1585, 1395, 1295, 1240, 1145, 995 cm-1 ; 1H-NMR (360 MHz, CH3OH-d4 : 3.47 (s, 3H, OCH3), 4.74 (d, 2H, CH2P+), 6.40 (dd, 1H), 6.62 (d, 1H), 6.73 (m, 1H), 7.56 to 7.72 (m, 12H), 7.87 (m, 3H) ppm]; yield 78% of the theoretical yield. to crystallise after approx. 30 minutes The reaction mixture is cooled to 0° stirred for a further one hour at that temperature the crystals are filtered off with suction

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a suspension of sodium borohydride (2.50 g, 65.8 mmol) in ethanol (100 mL) at 5° C. was added a solution of 2-hydroxy-5-methoxybenzaldehyde (10.00 g, 65.8 mmol) in ethanol (35 mL) dropwise. Upon completion of the addition the reaction mixture was allowed to stir for ten minutes then quenched by the dropwise addition of 10% aqueous acetic acid (75 mL). The ethanol was removed by concentration in vacuo and the resulting mixture poured into water (250 mL) and extracted with ethylacetate (3×100 mL). The combined extracts were washed sequentially with saturated sodium bicarbonate (50 mL), and brine (3×100 mL). The organic extract was dried (Na2SO4) and concentrated to afford a crude product (8.75 g). Trituration with hexane:ether (3:2, 25 mL) afforded 2-hydroxy-5-methoxybenzyl alcohol (7.00 g, 70%) as a white solid. Upon completion of the addition the reaction mixture then quenched by the dropwise addition of 10% aqueous acetic acid (75 mL) The ethanol was removed by concentration in vacuo the resulting mixture poured into water (250 mL) extracted with ethylacetate (3×100 mL) The combined extracts were washed sequentially with saturated sodium bicarbonate (50 mL), and brine (3×100 mL) The organic extract was dried (Na2SO4) concentrated to afford a crude product (8.75 g)

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: In the course of 30 minutes, at from 40° to 60°, 18 g of hydrogen chloride are introduced into a solution of 49.8 g of 2-hydroxy-5-methoxy-benzyl alcohol and 115.8 g of triphenylphosphane in 150 ml of acetonitrile. The reaction mixture is then stirred for 5 hours at 75°, the product beginning to crystallise after approx. 30 minutes. The reaction mixture is cooled to 0°, stirred for a further one hour and then at that temperature the crystals are filtered off with suction. [(2-Hydroxy-5-methoxy-phenyl)methyl]-triphenyl-phosphonium chloride is thus obtained in the form of colourless crystals [m.p.: 270° (decomposition); IR (KBr): 2990, 1585, 1395, 1295, 1240, 1145, 995 cm-1 ; 1H-NMR (360 MHz, CH3OH-d4 : 3.47 (s, 3H, OCH3), 4.74 (d, 2H, CH2P+), 6.40 (dd, 1H), 6.62 (d, 1H), 6.73 (m, 1H), 7.56 to 7.72 (m, 12H), 7.87 (m, 3H) ppm]; yield 78% of the theoretical yield. to crystallise after approx. 30 minutes The reaction mixture is cooled to 0° stirred for a further one hour at that temperature the crystals are filtered off with suction

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Under ice cooling, the solution of 5-methoxysalicylaldehyde (5 g) in ether (20 ml) was slowly added dropwise to the suspension of LiAlH4 (0.75 g) in ether (50 ml). After stirring at room temperature for 2 hours, another addition of LiAlH4 (0.5 g) was carried out under ice cooling, with subsequent stirring at room temperature for 30 minutes. To the reaction solution was added ice carefully, followed by sequential addition of 1N HCl and ether. After filtering off insoluble materials using Celite™, the ether layer was separated from the filtrate, and then, the aqueous phase was further extracted with ether. The combined ether layers were washed with saturated sodium chloride solution, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the residue was washed with ether-hexane and filtered to give the title compound (3.9 g; 77%). with subsequent stirring at room temperature for 30 minutes To the reaction solution was added ice carefully After filtering off insoluble materials the ether layer was separated from the filtrate the aqueous phase was further extracted with ether The combined ether layers were washed with saturated sodium chloride solution dried over anhydrous sodium sulfate The solvent was removed under reduced pressure the residue was washed with ether-hexane filtered

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: In the course of 30 minutes, at from 40° to 60°, 18 g of hydrogen chloride are introduced into a solution of 49.8 g of 2-hydroxy-5-methoxy-benzyl alcohol and 115.8 g of triphenylphosphane in 150 ml of acetonitrile. The reaction mixture is then stirred for 5 hours at 75°, the product beginning to crystallise after approx. 30 minutes. The reaction mixture is cooled to 0°, stirred for a further one hour and then at that temperature the crystals are filtered off with suction. [(2-Hydroxy-5-methoxy-phenyl)methyl]-triphenyl-phosphonium chloride is thus obtained in the form of colourless crystals [m.p.: 270° (decomposition); IR (KBr): 2990, 1585, 1395, 1295, 1240, 1145, 995 cm-1 ; 1H-NMR (360 MHz, CH3OH-d4 : 3.47 (s, 3H, OCH3), 4.74 (d, 2H, CH2P+), 6.40 (dd, 1H), 6.62 (d, 1H), 6.73 (m, 1H), 7.56 to 7.72 (m, 12H), 7.87 (m, 3H) ppm]; yield 78% of the theoretical yield. to crystallise after approx. 30 minutes The reaction mixture is cooled to 0° stirred for a further one hour at that temperature the crystals are filtered off with suction