ethyl 4-(2,3-dimethylphenoxy)butanoate

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:64.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of copper(II)sulfate pentahydrate (21.98 g, 88.06 mmol) and potassium persulfate (71.42 g, 264 mmol) in water (396 mL) was heated to 63-65° C. to obtain a blue colored solution. Then, a solution of 4-(2,3-dimethyl-phenoxy)-butyric acid ethyl ester (20.81 g, 88.06 mmol) in acetonitrile (220 mL) was added at the above temperature. The resulting light green solution was refluxed for 40 minutes. Then, the reaction mixture was cooled to ˜5° C. in order to precipitate most of the inorganic solids. The resulting solids were collected by filtration and the solid cake was washed with dichloromethane (1.0 L). The two layers of filtrate were separated and the aqueous layer was extracted with dichloromethane (200 mL). The combined organic extracts were washed with brine solution (150 mL) and the organic solution was dried over anhydrous magnesium sulfate. Filtration of the drying agent and the removal of the solvent gave a brown oil. The crude mixture was purified by using a Biotage (40L) column chromatography eluting with 5-10% ethyl acetate in hexanes to obtain 4-(2-formyl-3-methyl-phenoxy)-butyric acid ethyl ester (45.32 g, 94%) as a colorless oil: EI(+)-HRMS m/e calculated for C14H18O4 (M+)+ 250.1205, found 250.1202. to obtain a blue colored solution The resulting light green solution was refluxed for 40 minutes Then, the reaction mixture was cooled to ˜5° C. in order to precipitate most of the inorganic solids The resulting solids were collected by filtration the solid cake was washed with dichloromethane (1.0 L) The two layers of filtrate were separated the aqueous layer was extracted with dichloromethane (200 mL) The combined organic extracts were washed with brine solution (150 mL) the organic solution was dried over anhydrous magnesium sulfate Filtration of the drying agent the removal of the solvent gave a brown oil The crude mixture was purified eluting with 5-10% ethyl acetate in hexanes

反応条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of 2,3-dimethylphenol (25 g, 204 mmol) in DMSO (205 Ml) was added 4-bromo-butyric acid ethyl ester (40.96 g, 210 mmol) and lithium hydride (2.0 g, 250 mmol) at room temperature. The resulting light brown solution was stirred for 2 days. Then, the reaction mixture was cooled to 0° C. and water (200 Ml) was added slowly. The organic compound was extracted into hexanes (2×200 Ml). The combined organic extracts were washed with brine solution (150 Ml) and the organic solution was dried over anhydrous magnesium sulfate. Filtration of the drying agent and the removal of the solvent gave light brown oil. The crude mixture was purified by using a Biotage (40L) column chromatography eluting with 5% ethyl acetate in hexanes to isolate 4-(2,3-dimethyl-phenoxy)-butyric acid ethyl ester (45.32 g, 94%) as a colorless oil: ES(+)-HRMS m/e calculated for C14H20O3 (M+)+ 236.1412, found 236.1419. The organic compound was extracted into hexanes (2×200 Ml) The combined organic extracts were washed with brine solution (150 Ml) the organic solution was dried over anhydrous magnesium sulfate Filtration of the drying agent the removal of the solvent gave light brown oil The crude mixture was purified eluting with 5% ethyl acetate in hexanes

反応条件: temp:64.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of copper(II) sulfate pentahydrate (21.98 g, 88.06 mmol) and potassium persulfate (71.42 g, 264 mmol) in water (396 mL) was heated to 63-65° C. to obtain a blue colored solution. Then, a solution of 4-(2,3-dimethyl-phenoxy)-butyric acid ethyl ester (20.81 g, 88.06 mmol) in acetonitrile (220 mL) was added at the above temperature. The resulting light green solution was refluxed for 40 minutes. Then, the reaction mixture was cooled to ˜5° C. in order to precipitate most of the inorganic solids. The resulting solids were collected by filtration and the solid cake was washed with dichloromethane (1.0 L). The two layers of filtrate were separated and the aqueous layer was extracted with dichloromethane (200 mL). The combined organic extracts were washed with brine solution (150 mL) and the organic solution was dried over anhydrous magnesium sulfate. Filtration of the drying agent and the removal of the solvent gave a brown oil. The crude mixture was purified by using a Biotage™ (40 L) column chromatography eluting with 5-10% ethyl acetate in hexanes to obtain 4-(2-formyl-3-methyl-phenoxy)-butyric acid ethyl ester (45.32 g, 94%) as a colorless oil: EI(+)-HRMS m/e calculated for C14H18O4 (M+)+ 250.1205, found 250.1202. to obtain a blue colored solution The resulting light green solution was refluxed for 40 minutes Then, the reaction mixture was cooled to ˜5° C. in order to precipitate most of the inorganic solids The resulting solids were collected by filtration the solid cake was washed with dichloromethane (1.0 L) The two layers of filtrate were separated the aqueous layer was extracted with dichloromethane (200 mL) The combined organic extracts were washed with brine solution (150 mL) the organic solution was dried over anhydrous magnesium sulfate Filtration of the drying agent the removal of the solvent gave a brown oil The crude mixture was purified eluting with 5-10% ethyl acetate in hexanes

反応条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of 2,3-dimethylphenol (25 g, 204 mmol) in DMSO (205 mL) was added 4-bromo-butyric acid ethyl ester (40.96 g, 210 mmol) and lithium hydride (2.0 g, 250 mmol) at room temperature. The resulting light brown solution was stirred for 2 days. Then, the reaction mixture was cooled to 0° C. and water (200 mL) was added slowly. The organic compound was extracted into hexanes (2×200 mL). The combined organic extracts were washed with brine solution (150 mL) and the organic solution was dried over anhydrous magnesium sulfate. Filtration of the drying agent and the removal of the solvent gave light brown oil. The crude mixture was purified by using a Biotage™ (40 L) column chromatography eluting with 5% ethyl acetate in hexanes to isolate 4-(2,3-dimethyl-phenoxy)-butyric acid ethyl ester (45.32 g, 94%) as a colorless oil: ES(+)-HRMS m/e calculated for C14H20O3 (M+)+ 236.1412, found 236.1419. The organic compound was extracted into hexanes (2×200 mL) The combined organic extracts were washed with brine solution (150 mL) the organic solution was dried over anhydrous magnesium sulfate Filtration of the drying agent the removal of the solvent gave light brown oil The crude mixture was purified eluting with 5% ethyl acetate in hexanes

反応条件: temp:64.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of copper(II) sulfate pentahydrate (21.98 g, 88.06 mmol) and potassium persulfate (71.42 g, 264 mmol) in water (396 mL) was heated to 63-65° C. to obtain a blue colored solution. Then, a solution of 4-(2,3-dimethyl-phenoxy)-butyric acid ethyl ester (20.81 g, 88.06 mmol) in acetonitrile (220 mL) was added at the above temperature. The resulting light green solution was refluxed for 40 minutes. Then, the reaction mixture was cooled to ˜5° C. in order to precipitate most of the inorganic solids. The resulting solids were collected by filtration and the solid cake was washed with dichloromethane (1.0 L). The two layers of filtrate were separated and the aqueous layer was extracted with dichloromethane (200 mL). The combined organic extracts were washed with brine solution (150 mL) and the organic solution was dried over anhydrous magnesium sulfate. Filtration of the drying agent and the removal of the solvent gave a brown oil. The crude mixture was purified by using a Biotage™ (40 L) column chromatography eluting with 5-10% ethyl acetate in hexanes to obtain 4-(2-formyl-3-methyl-phenoxy)-butyric acid ethyl ester (45.32 g, 94%) as a colorless oil: EI(+)-HRMS m/e calculated for C14H18O4 (M+)+ 250.1205. found 250.1202. to obtain a blue colored solution The resulting light green solution was refluxed for 40 minutes Then, the reaction mixture was cooled to ˜5° C. in order to precipitate most of the inorganic solids The resulting solids were collected by filtration the solid cake was washed with dichloromethane (1.0 L) The two layers of filtrate were separated the aqueous layer was extracted with dichloromethane (200 mL) The combined organic extracts were washed with brine solution (150 mL) the organic solution was dried over anhydrous magnesium sulfate Filtration of the drying agent the removal of the solvent gave a brown oil The crude mixture was purified eluting with 5-10% ethyl acetate in hexanes

反応条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of 2,3-dimethylphenol (25 g, 204 mmol) in DMSO (205 mL) was added 4-bromo-butyric acid ethyl ester (40.96 g, 210 mmol) and lithium hydride (2.0 g, 250 mmol) at room temperature. The resulting light brown solution was stirred for 2 days. Then, the reaction mixture was cooled to 0° C. and water (200 mL) was added slowly. The organic compound was extracted into hexanes (2×200 mL). The combined organic extracts were washed with brine solution (150 mL) and the organic solution was dried over anhydrous magnesium sulfate. Filtration of the drying agent and the removal of the solvent gave light brown oil. The crude mixture was purified by using a Biotage™ (40 L) column chromatography eluting with 5% ethyl acetate in hexanes to isolate 4-(2,3-dimethyl-phenoxy)-butyric acid ethyl ester (45.32 g, 94%) as a colorless oil: ES(+)-HRMS m/e calculated for C14H20O3 (M+)+ 236.1412. found 236.1419. The organic compound was extracted into hexanes (2×200 mL) The combined organic extracts were washed with brine solution (150 mL) the organic solution was dried over anhydrous magnesium sulfate Filtration of the drying agent the removal of the solvent gave light brown oil The crude mixture was purified eluting with 5% ethyl acetate in hexanes

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:64.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of copper(II)sulfate pentahydrate (21.98 g, 88.06 mmol) and potassium persulfate (71.42 g, 264 mmol) in water (396 mL) was heated to 63-65° C. to obtain a blue colored solution. Then, a solution of 4-(2,3-dimethyl-phenoxy)-butyric acid ethyl ester (20.81 g, 88.06 mmol) in acetonitrile (220 mL) was added at the above temperature. The resulting light green solution was refluxed for 40 minutes. Then, the reaction mixture was cooled to ˜5° C. in order to precipitate most of the inorganic solids. The resulting solids were collected by filtration and the solid cake was washed with dichloromethane (1.0 L). The two layers of filtrate were separated and the aqueous layer was extracted with dichloromethane (200 mL). The combined organic extracts were washed with brine solution (150 mL) and the organic solution was dried over anhydrous magnesium sulfate. Filtration of the drying agent and the removal of the solvent gave a brown oil. The crude mixture was purified by using a Biotage (40L) column chromatography eluting with 5-10% ethyl acetate in hexanes to obtain 4-(2-formyl-3-methyl-phenoxy)-butyric acid ethyl ester (45.32 g, 94%) as a colorless oil: EI(+)-HRMS m/e calculated for C14H18O4 (M+)+ 250.1205, found 250.1202. to obtain a blue colored solution The resulting light green solution was refluxed for 40 minutes Then, the reaction mixture was cooled to ˜5° C. in order to precipitate most of the inorganic solids The resulting solids were collected by filtration the solid cake was washed with dichloromethane (1.0 L) The two layers of filtrate were separated the aqueous layer was extracted with dichloromethane (200 mL) The combined organic extracts were washed with brine solution (150 mL) the organic solution was dried over anhydrous magnesium sulfate Filtration of the drying agent the removal of the solvent gave a brown oil The crude mixture was purified eluting with 5-10% ethyl acetate in hexanes

反応条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of 2,3-dimethylphenol (25 g, 204 mmol) in DMSO (205 Ml) was added 4-bromo-butyric acid ethyl ester (40.96 g, 210 mmol) and lithium hydride (2.0 g, 250 mmol) at room temperature. The resulting light brown solution was stirred for 2 days. Then, the reaction mixture was cooled to 0° C. and water (200 Ml) was added slowly. The organic compound was extracted into hexanes (2×200 Ml). The combined organic extracts were washed with brine solution (150 Ml) and the organic solution was dried over anhydrous magnesium sulfate. Filtration of the drying agent and the removal of the solvent gave light brown oil. The crude mixture was purified by using a Biotage (40L) column chromatography eluting with 5% ethyl acetate in hexanes to isolate 4-(2,3-dimethyl-phenoxy)-butyric acid ethyl ester (45.32 g, 94%) as a colorless oil: ES(+)-HRMS m/e calculated for C14H20O3 (M+)+ 236.1412, found 236.1419. The organic compound was extracted into hexanes (2×200 Ml) The combined organic extracts were washed with brine solution (150 Ml) the organic solution was dried over anhydrous magnesium sulfate Filtration of the drying agent the removal of the solvent gave light brown oil The crude mixture was purified eluting with 5% ethyl acetate in hexanes

反応条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of 2,3-dimethylphenol (25 g, 204 mmol) in DMSO (205 Ml) was added 4-bromo-butyric acid ethyl ester (40.96 g, 210 mmol) and lithium hydride (2.0 g, 250 mmol) at room temperature. The resulting light brown solution was stirred for 2 days. Then, the reaction mixture was cooled to 0° C. and water (200 Ml) was added slowly. The organic compound was extracted into hexanes (2×200 Ml). The combined organic extracts were washed with brine solution (150 Ml) and the organic solution was dried over anhydrous magnesium sulfate. Filtration of the drying agent and the removal of the solvent gave light brown oil. The crude mixture was purified by using a Biotage (40L) column chromatography eluting with 5% ethyl acetate in hexanes to isolate 4-(2,3-dimethyl-phenoxy)-butyric acid ethyl ester (45.32 g, 94%) as a colorless oil: ES(+)-HRMS m/e calculated for C14H20O3 (M+)+ 236.1412, found 236.1419. The organic compound was extracted into hexanes (2×200 Ml) The combined organic extracts were washed with brine solution (150 Ml) the organic solution was dried over anhydrous magnesium sulfate Filtration of the drying agent the removal of the solvent gave light brown oil The crude mixture was purified eluting with 5% ethyl acetate in hexanes