methyl 2-phenylbutanoate

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

Procedure: To 15.4 ml of diisopropylamine in 400 ml of dry tetrahydrofuran at -20° to -30° under nitrogen atmosphere was added dropwise with stirring 64.3 ml of a 1.71 M solution of butyllithium in hexane. After stirring 15 min., the mixture was cooled to -70° and a solution of 17.8 g of methyl 2-phenylbutyrate in 100 ml of tetrahydrofuran was added dropwise. After stirring 30 min., a solution of 19.9 ml of allyl bromide in 50 ml tetrahydrofuran was added dropwise; the mixture was stirred and allowed to warm to room temperature overnight. After decomposing with methanol, the reaction mixture was concentrated in vacuo and the residue dissolved in diethyl ether. The ether solution was washed successively with dilute hydrochloric acid, water, dilute sodium bicarbonate, and saturated sodium chloride solution, then dried over anhydrous potassium carbonate and concentrated in vacuo. Distillation of the residue yielded 20.2 g of the title compound as a water-white oil, b.p. 84°-86°/0.45 mm, having the following elemental analysis: the mixture was cooled to -70° After stirring 30 min. the mixture was stirred the reaction mixture was concentrated in vacuo the residue dissolved in diethyl ether The ether solution was washed successively with dilute hydrochloric acid, water, dilute sodium bicarbonate, and saturated sodium chloride solution dried over anhydrous potassium carbonate concentrated in vacuo Distillation of the residue

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

Procedure: To 15.4 ml of diisopropylamine in 400 ml of dry tetrahydrofuran at -20° to -30° under nitrogen atmosphere was added dropwise with stirring 64.3 ml of a 1.71 M solution of butyllithium in hexane. After stirring 15 min., the mixture was cooled to -70° and a solution of 17.8 g of methyl 2-phenylbutyrate in 100 ml of tetrahydrofuran was added dropwise. After stirring 30 min., a solution of 19.9 ml of allyl bromide in 50 ml tetrahydrofuran was added dropwise; the mixture was stirred and allowed to warm to room temperature overnight. After decomposing with methanol, the reaction mixture was concentrated in vacuo and the residue dissolved in diethyl ether. The ether solution was washed successively with dilute hydrochloric acid, water, dilute sodium bicarbonate, and saturated sodium chloride solution, then dried over anhydrous potassium carbonate and concentrated in vacuo. Distillation of the residue yielded 20.2 g of the title compound as a water-white oil, b.p. 84°-86°/0.45 mm, having the following elemental analysis: the mixture was cooled to -70° After stirring 30 min. the mixture was stirred the reaction mixture was concentrated in vacuo the residue dissolved in diethyl ether The ether solution was washed successively with dilute hydrochloric acid, water, dilute sodium bicarbonate, and saturated sodium chloride solution dried over anhydrous potassium carbonate concentrated in vacuo Distillation of the residue

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

Procedure: To 102 g. of 2-phenylbutyric acid dissolved in 1 liter of methanol was added 2 ml of thionyl chloride. The solution was allowed to stand at room temperature overnight. The solvent was removed in vacuo to yield an oil which was dissolved in diethyl ether, washed successively with dilute sodium bicarbonate solution and saturated sodium chloride solution, dried over anhydrous potassium carbonate, and concentrated in vacuo. Distillation yielded 101 g of the title compound as a water-white oil, b.p. 62°-65°/0.5 mm, having the following elemental analysis: The solvent was removed in vacuo to yield an oil which washed successively with dilute sodium bicarbonate solution and saturated sodium chloride solution dried over anhydrous potassium carbonate concentrated in vacuo Distillation

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

Procedure: To 102 g. of 2-phenylbutyric acid dissolved in 1 liter of methanol was added 2 ml of thionyl chloride. The solution was allowed to stand at room temperature overnight. The solvent was removed in vacuo to yield an oil which was dissolved in diethyl ether, washed successively with dilute sodium bicarbonate solution and saturated sodium chloride solution, dried over anhydrous potassium carbonate, and concentrated in vacuo. Distillation yielded 101 g of the title compound as a water-white oil, b.p. 62°-65°/0.5 mm, having the following elemental analysis: The solvent was removed in vacuo to yield an oil which washed successively with dilute sodium bicarbonate solution and saturated sodium chloride solution dried over anhydrous potassium carbonate concentrated in vacuo Distillation

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

Procedure: Into the cathode chamber of an electrolytic cell divided with an ion-exchange resin diaphragm was placed a solution of 10 mmols of methyl phenylacetate, 12 mmols of ethyl methanesulfonate and 1.0 g of tetraethylammonium tosylate in 30 ml of anhydrous dimethylformamide. And the anode chamber was provided with a solution of 1.0 g of tetraethylammonium tosylate in 10 ml of anhydrous dimethylformamide. Constant current electrolysis was performed at 0.2 A/cm2 with use of platinum for the cathode and carbon for the anode. After passing 1.5 F of electricity per mol of the methyl phenylacetate through the solution at 5 to 10 C, the cathode solution was added to a saturated aqueous solution of ammonium chloride and the mixture was extracted twice with ether. The ether was distilled off and the residue was purified by silica gel column chromatography using hexane-ethyl acetate (10:1), giving methyl α-ethylphenylacetate in a yield of 77% and α-ethylphenylacetic acid in a yield of 13%. The spectral data of the ester were as follows. the mixture was extracted twice with ether The ether was distilled off the residue was purified by silica gel column chromatography

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

Procedure: 2-Phenylbutyric acid (10 g, 61 mmole) was dissolved in methanol (30 ml) treated with concentrated HCl (1 ml) and heated at reflux for 20 hours. The heating was stopped and the reaction mixture cooled to room temperature. The solvent was removed in vacuo and the oily residue was treated with ethyl acetate (100 ml). The organic layer was washed with saturated sodium bicarbonate solution and saturated sodium chloride solution, dried (Na2SO4), filtered and concentrated in vacuo to give the title compound as a clear oil. Yield 10.61 g (97%). 1H NMR (300 MHz, DMSO-d6): δ ppm 0.81 (t, J=7.35 Hz, 3H) 1.69 (m, 1H) 1.98 (m, 1H) 3.53 (d, J=7.35 Hz, 1H) 3.58 (s, 3H) 7.30 (m, 5H). heated at reflux for 20 hours The solvent was removed in vacuo the oily residue was treated with ethyl acetate (100 ml) The organic layer was washed with saturated sodium bicarbonate solution and saturated sodium chloride solution dried (Na2SO4) filtered concentrated in vacuo

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

Procedure: To 15.4 ml of diisopropylamine in 400 ml of dry tetrahydrofuran at -20° to -30° under nitrogen atmosphere was added dropwise with stirring 64.3 ml of a 1.71 M solution of butyllithium in hexane. After stirring 15 min., the mixture was cooled to -70° and a solution of 17.8 g of methyl 2-phenylbutyrate in 100 ml of tetrahydrofuran was added dropwise. After stirring 30 min., a solution of 19.9 ml of allyl bromide in 50 ml tetrahydrofuran was added dropwise; the mixture was stirred and allowed to warm to room temperature overnight. After decomposing with methanol, the reaction mixture was concentrated in vacuo and the residue dissolved in diethyl ether. The ether solution was washed successively with dilute hydrochloric acid, water, dilute sodium bicarbonate, and saturated sodium chloride solution, then dried over anhydrous potassium carbonate and concentrated in vacuo. Distillation of the residue yielded 20.2 g of the title compound as a water-white oil, b.p. 84°-86°/0.45 mm, having the following elemental analysis: the mixture was cooled to -70° After stirring 30 min. the mixture was stirred the reaction mixture was concentrated in vacuo the residue dissolved in diethyl ether The ether solution was washed successively with dilute hydrochloric acid, water, dilute sodium bicarbonate, and saturated sodium chloride solution dried over anhydrous potassium carbonate concentrated in vacuo Distillation of the residue

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

Procedure: To 102 g. of 2-phenylbutyric acid dissolved in 1 liter of methanol was added 2 ml of thionyl chloride. The solution was allowed to stand at room temperature overnight. The solvent was removed in vacuo to yield an oil which was dissolved in diethyl ether, washed successively with dilute sodium bicarbonate solution and saturated sodium chloride solution, dried over anhydrous potassium carbonate, and concentrated in vacuo. Distillation yielded 101 g of the title compound as a water-white oil, b.p. 62°-65°/0.5 mm, having the following elemental analysis: The solvent was removed in vacuo to yield an oil which washed successively with dilute sodium bicarbonate solution and saturated sodium chloride solution dried over anhydrous potassium carbonate concentrated in vacuo Distillation

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

Procedure: 2-Phenylbutyric acid (10 g, 61 mmole) was dissolved in methanol (30 ml) treated with concentrated HCl (1 ml) and heated at reflux for 20 hours. The heating was stopped and the reaction mixture cooled to room temperature. The solvent was removed in vacuo and the oily residue was treated with ethyl acetate (100 ml). The organic layer was washed with saturated sodium bicarbonate solution and saturated sodium chloride solution, dried (Na2SO4), filtered and concentrated in vacuo to give the title compound as a clear oil. Yield 10.61 g (97%). 1H NMR (300 MHz, DMSO-d6): δ ppm 0.81 (t, J=7.35 Hz, 3 H) 1.69 m, 1 H) 1.98 (m, 1 H) 3.53 (d, J=7.35 Hz, 1 H) 3.58 (s, 3 H) 7.30 m, 5 H). heated at reflux for 20 hours The solvent was removed in vacuo the oily residue was treated with ethyl acetate (100 ml) The organic layer was washed with saturated sodium bicarbonate solution and saturated sodium chloride solution dried (Na2SO4) filtered concentrated in vacuo

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

Procedure: 2-Phenylbutyric acid (10 g, 61 mmole) was dissolved in methanol (30 ml) treated with concentrated HCl (1 ml) and heated at reflux for 20 hours. The heating was stopped and the reaction mixture cooled to room temperature. The solvent was removed in vacuo and the oily residue was treated with ethyl acetate (100 ml). The organic layer was washed with saturated sodium bicarbonate solution and saturated sodium chloride solution, dried (Na2SO4), filtered and concentrated in vacuo to give the title compound as a clear oil. Yield 10.61 g (97%). 1H NMR (300 MHz, DMSO-d6): δ ppm 0.81 (t, J=7.35 Hz, 3 H) 1.69 m, 1 H) 1.98 (m, 1 H) 3.53 (d, J=7.35 Hz, 1 H) 3.58 (s, 3 H) 7.30 m, 5 H). heated at reflux for 20 hours The solvent was removed in vacuo the oily residue was treated with ethyl acetate (100 ml) The organic layer was washed with saturated sodium bicarbonate solution and saturated sodium chloride solution dried (Na2SO4) filtered concentrated in vacuo

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

Procedure: Into the cathode chamber of an electrolytic cell divided with an ion-exchange resin diaphragm was placed a solution of 10 mmols of methyl phenylacetate, 12 mmols of ethyl methanesulfonate and 1.0 g of tetraethylammonium tosylate in 30 ml of anhydrous dimethylformamide. And the anode chamber was provided with a solution of 1.0 g of tetraethylammonium tosylate in 10 ml of anhydrous dimethylformamide. Constant current electrolysis was performed at 0.2 A/cm2 with use of platinum for the cathode and carbon for the anode. After passing 1.5 F of electricity per mol of the methyl phenylacetate through the solution at 5 to 10 C, the cathode solution was added to a saturated aqueous solution of ammonium chloride and the mixture was extracted twice with ether. The ether was distilled off and the residue was purified by silica gel column chromatography using hexane-ethyl acetate (10:1), giving methyl α-ethylphenylacetate in a yield of 77% and α-ethylphenylacetic acid in a yield of 13%. The spectral data of the ester were as follows. the mixture was extracted twice with ether The ether was distilled off the residue was purified by silica gel column chromatography

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

Procedure: 2-Phenylbutyric acid (10 g, 61 mmole) was dissolved in methanol (30 ml) treated with concentrated HCl (1 ml) and heated at reflux for 20 hours. The heating was stopped and the reaction mixture cooled to room temperature. The solvent was removed in vacuo and the oily residue was treated with ethyl acetate (100 ml). The organic layer was washed with saturated sodium bicarbonate solution and saturated sodium chloride solution, dried (Na2SO4), filtered and concentrated in vacuo to give the title compound as a clear oil. Yield 10.61 g (97%). 1H NMR (300 MHz, DMSO-d6): δ ppm 0.81 (t, J=7.35 Hz, 3H) 1.69 (m, 1H) 1.98 (m, 1H) 3.53 (d, J=7.35 Hz, 1H) 3.58 (s, 3H) 7.30 (m, 5H). heated at reflux for 20 hours The solvent was removed in vacuo the oily residue was treated with ethyl acetate (100 ml) The organic layer was washed with saturated sodium bicarbonate solution and saturated sodium chloride solution dried (Na2SO4) filtered concentrated in vacuo