methyl 3-hydroxy-2-phenylpropanoate

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: A nitrogen purged 500 mL three-neck flask was charged with sodium bicarbonate (1.05 g; 0.013 mole), paraformaldehyde (17.37 g; 0.55 mole) and dimethyl sulfoxide (100 mL). Methyl phenylacetate (75.09 g; 0.5 mole) was added and rinsed in with dimethylsulfoxide (50 mL). The slurry was stirred magnetically and the temperature rose from 22° C. to 34° C. over 40 minutes. The temperature remained at 33°-35° C. for about one hour, after which the temperature was raised to 45°-46° C. and held for 12 hours. The reaction mixture was allowed to cool with stirring for about seven hours. A solution of tartaric acid (1.88 g) in dimethylsulfoxide (6 mL) was added, and the solvent was distilled at pot temperature 45° C. to 88° C. at 0 25 mm Hg. The distillate (168.11 g) was retained. The pale yellow oily residue (97.79 g) which contained a small amount of white solid(sodium hydrogen tartrate) was filtered, then fractionally distilled to give a main cut (59.1 g) of methyl tropate b.p. 106°-112° C. (0.2 mm. Hg). A nitrogen purged 500 mL three-neck flask rinsed in with dimethylsulfoxide (50 mL) The temperature remained at 33°-35° C. for about one hour after which the temperature was raised to 45°-46° C. held for 12 hours to cool with stirring for about seven hours A solution of tartaric acid (1.88 g) in dimethylsulfoxide (6 mL) was added the solvent was distilled at pot temperature 45° C. to 88° C. at 0 25 mm Hg was filtered fractionally distilled

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

Procedure: A nitrogen purged 500 mL three-neck flask was charged with sodium bicarbonate (1.05 g; 0.013 mole), paraformaldehyde (17.37 g; 0.55 mole) and dimethyl sulfoxide (100 mL). Methyl phenylacetate (75.09 g; 0.5 mole) was added and rinsed in with dimethylsulfoxide (50 mL). The slurry was stirred magnetically and the temperature rose from 22° C. to 34° C. over 40 minutes. The temperature remained at 33°-34° C. for about one hour, after which the temperature was raised to 45°-46° C. and held for 12 hours. The reaction mixture was allowed to cool with stirring for about seven hours. A solution of anhydrous oxalic acid (1.13 g; 0.013 mole) in dimethylsulfoxide (6 mL) was added, and the solvent was distilled at pot temperature 45° C. to 100° C. at 0.05 mm Hg. The distillate (153.6 g) was retained. The pale yellow oily residue of crude methyl tropate (112.82 g) contained a small amount of white solid (sodium hydrogen oxalate). A nitrogen purged 500 mL three-neck flask rinsed in with dimethylsulfoxide (50 mL) The temperature remained at 33°-34° C. for about one hour after which the temperature was raised to 45°-46° C. held for 12 hours to cool with stirring for about seven hours the solvent was distilled at pot temperature 45° C. to 100° C. at 0.05 mm Hg

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

Procedure: A three necked one-liter flask equipped with a drying tube, a thermometer and a stopper was flame-dried, cooled and then charged with sodium bicarbonate (2.1 g; 0.025 mole), paraformaldehyde (34.74 g; 1.1 mole) and 300 mL of dimethylsulfoxide (DMSO). The air in the flask was purged with dry nitrogen and methyl phenylacetate (150:18 g; 1 mole) was added in one portion. Residual ester was washed into the flask using dry DMSO (5 mL). The slurry was then stirred magnetically (initial temperature 22°-23° C.) and the temperature rose slowly over one hour to 33° C. The temperature remained at about 32°-33° C. for 1.5 hrs. at which time the reaction liquid was almost a clear solution. The temperature was then raised to 45°-46° C. over 30 min. and kept at this temperature for 12 hrs. The solution was then allowed to cool and left at room temperature for 9 hrs. The reaction mixture was clear and essentially colorless with only a small amount of a white solid appearing at the bottom of the flask. NMR analysis of the solution indicated approximately an 80% yield of methyl tropate. A three necked one-liter flask equipped with a drying tube a thermometer and a stopper was flame-dried cooled was added in one portion Residual ester was washed into the flask at which time the reaction liquid The temperature was then raised to 45°-46° C. over 30 min. kept at this temperature for 12 hrs to cool left at room temperature for 9 hrs

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

Procedure: A three necked one-liter flask equipped with a drying tube, a thermometer and a stopper was flame-dried, cooled and then charged with sodium bicarbonate (2.1 g; 0.025 mole), paraformaldehyde (34.74 g; 1.1 mole) and 300 mL of dimethylsulfoxide (DMSO). The air in the flask was purged with dry nitrogen and methyl phenylacetate (150:18 g; 1 mole) was added in one portion. Residual ester was washed into the flask using dry DMSO (5 mL). The slurry was then stirred magnetically (initial temperature 22°-23° C.) and the temperature rose slowly over one hour to 33° C. The temperature remained at about 32°-33° C. for 1.5 hrs. at which time the reaction liquid was almost a clear solution. The temperature was then raised to 45°-46° C. over 30 min. and kept at this temperature for 12 hrs. The solution was then allowed to cool and left at room temperature for 9 hrs. The reaction mixture was clear and essentially colorless with only a small amount of a white solid appearing at the bottom of the flask. NMR analysis of the solution indicated approximately an 80% yield of methyl tropate. A three necked one-liter flask equipped with a drying tube a thermometer and a stopper was flame-dried cooled was added in one portion Residual ester was washed into the flask at which time the reaction liquid The temperature was then raised to 45°-46° C. over 30 min. kept at this temperature for 12 hrs to cool left at room temperature for 9 hrs

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

Procedure: A three necked one-liter flask equipped with a drying tube, a thermometer and a stopper was flame-dried, cooled and then charged with sodium bicarbonate (2.1 g; 0.025 mole), paraformaldehyde (34.74 g; 1.1 mole) and 300 mL of dimethylsulfoxide (DMSO). The air in the flask was purged with dry nitrogen and methyl phenylacetate (150:18 g; 1 mole) was added in one portion. Residual ester was washed into the flask using dry DMSO (5 mL). The slurry was then stirred magnetically (initial temperature 22°-23° C.) and the temperature rose slowly over one hour to 33° C. The temperature remained at about 32°-33° C. for 1.5 hrs. at which time the reaction liquid was almost a clear solution. The temperature was then raised to 45°-46° C. over 30 min. and kept at this temperature for 12 hrs. The solution was then allowed to cool and left at room temperature for 9 hrs. The reaction mixture was clear and essentially colorless with only a small amount of a white solid appearing at the bottom of the flask. NMR analysis of the solution indicated approximately an 80% yield of methyl tropate. A three necked one-liter flask equipped with a drying tube a thermometer and a stopper was flame-dried cooled was added in one portion Residual ester was washed into the flask at which time the reaction liquid The temperature was then raised to 45°-46° C. over 30 min. kept at this temperature for 12 hrs to cool left at room temperature for 9 hrs

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

Procedure: To a solution of tropic acid (5.0 g, 30 mmol) in toluene:CH2Cl2 (150 mL; 2:1) was added DBU (4.6 g; 30 mmol), followed by MeI (4.3 g; 30 mmol). The mixture was stirred overnight, water was added and the phases were allowed to separate. The water phase was extracted with ether, and the combined organic phase was washed with NaHCO3/aq, HCl/aq and water, dried (Na2SO4) and concentrated to yield 0.95 g (18%) of the sub-title compound. to separate The water phase was extracted with ether the combined organic phase was washed with NaHCO3/aq, HCl/aq and water dried (Na2SO4) concentrated

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

Procedure: A nitrogen purged 500 mL three-neck flask was charged with sodium bicarbonate (1.05 g; 0.013 mole), paraformaldehyde (17.37 g; 0.55 mole) and dimethyl sulfoxide (100 mL). Methyl phenylacetate (75.09 g; 0.5 mole) was added and rinsed in with dimethylsulfoxide (50 mL). The slurry was stirred magnetically and the temperature rose from 22° C. to 34° C. over 40 minutes. The temperature remained at 33°-35° C. for about one hour, after which the temperature was raised to 45°-46° C. and held for 12 hours. The reaction mixture was allowed to cool with stirring for about seven hours. A solution of tartaric acid (1.88 g) in dimethylsulfoxide (6 mL) was added, and the solvent was distilled at pot temperature 45° C. to 88° C. at 0.25 mm Hg. The distillate g) was retained. The pale yellow oily residue (97.79 g) which contained a small amount of white solid(sodium hydrogen tartrate) was filtered, then fractionally distilled to give a main cut (59.1 g) of methyl tropate b.p. 106°-112° C. (0.2 mm. Hg). A nitrogen purged 500 mL three-neck flask rinsed in with dimethylsulfoxide (50 mL) The temperature remained at 33°-35° C. for about one hour after which the temperature was raised to 45°-46° C. held for 12 hours to cool with stirring for about seven hours A solution of tartaric acid (1.88 g) in dimethylsulfoxide (6 mL) was added the solvent was distilled at pot temperature 45° C. to 88° C. at 0.25 mm Hg was filtered fractionally distilled