3-methylheptanoic acid

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: Under argon atmosphere, to a solution of sodium metal (70.6 g, 3.07 mol) in absolute ethanol (900 ml) was added ethyl malonate (510 g, 3.18 mol) with stirring. Further, 2-bromohexane (475 g, 2.88 mol) was added dropwise gradually and, after sodium bromide was precipitated, in such a rate that ethanol was slowly refluxed. After addition reflux was continued for 4 hours. After cooling the mixture to room temperature 50% aqueous potassium hydroxide solution (843 g) was added dropwise and the reaction mixture was refluxed for 5 hours. Ethanol was distilled off and the residue was neutralized with concentrated hydrochloric acid (600 ml). The resulting solution was then extracted with ether (one liter×3) and the extracts were dried over anhydrous sodium sulfate. After concentration, the residue was heated at 130° C. for 2 hours and at 180° C. for 2.5 hours. The distillation of the residue under reduced pressure gave dl-3-methylheptanoic acid (310 g, 2.15 mol, 75%, b.p.: 124°-125° C./25 mmHg). after sodium bromide was precipitated in such a rate that ethanol was slowly refluxed After addition reflux was added dropwise the reaction mixture was refluxed for 5 hours Ethanol was distilled off The resulting solution was then extracted with ether (one liter×3) the extracts were dried over anhydrous sodium sulfate After concentration the residue was heated at 130° C. for 2 hours and at 180° C. for 2.5 hours The distillation of the residue under reduced pressure

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

実験手順: Under argon atmosphere, to a solution of sodium metal (70.6 g, 3.07 mol) in absolute ethanol (900 ml) was added ethyl malonate (510 g, 3.18 mol) with stirring. Further, 2-bromohexane (475 g, 2.88 mol) was added dropwise gradually and, after sodium bromide was precipitated, in such a rate that ethanol was slowly refluxed. After addition reflux was continued for 4 hours. After cooling the mixture to room temperature 50% aqueous potassium hydroxide solution (843 g) was added dropwise and the reaction mixture was refluxed for 5 hours. Ethanol was distilled off and the residue was neutralized with concentrated hydrochloric acid (600 ml). The resulting solution was then extracted with ether (one liter×3) and the extracts were dried over anhydrous sodium sulfate. After concentration, the residue was heated at 130° C. for 2 hours and at 180° C. for 2.5 hours. The distillation of the residue under reduced pressure gave dl-3-methylheptanoic acid (310 g, 2.15 mol, 75%, b.p.: 124°-125° C./25 mmHg). after sodium bromide was precipitated in such a rate that ethanol was slowly refluxed After addition reflux was added dropwise the reaction mixture was refluxed for 5 hours Ethanol was distilled off The resulting solution was then extracted with ether (one liter×3) the extracts were dried over anhydrous sodium sulfate After concentration the residue was heated at 130° C. for 2 hours and at 180° C. for 2.5 hours The distillation of the residue under reduced pressure

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

実験手順: In this preparation 2 ml. of 30% aqueous potassium hydroxide is admixed with 0.1 mole of exobicyclo[3.1.0]hex-2-yl acetamide in 20 ml. of ethanol and warmed to 70° C and stirred at this temperature until no more ammonia evolves. The ethanol solvent is then removed by evaporation under vacuum and the residue poured into 100 ml. of water and extracted three times with ethyl ether. The aqueous solution is acidified to about pH 2 with 5N aqueous hydrochloric acid and then extracted three times with ethyl ether. The ethyl ether extracts are combined and dried over anhydrous magnesium sulfate, filtered and the filtrate evaporated under vacuum to remove the ethyl ether, affording exobicyclo[3.1.0]hex-2-yl acetic acid as a residue. In this preparation 2 ml The ethanol solvent is then removed by evaporation under vacuum the residue poured into 100 ml of water and extracted three times with ethyl ether extracted three times with ethyl ether dried over anhydrous magnesium sulfate filtered the filtrate evaporated under vacuum to remove the ethyl ether

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

実験手順: In this preparation 2 ml. of 30% aqueous potassium hydroxide is admixed with 0.1 mole of exobicyclo[3.1.0]hex-2-yl acetamide in 20 ml. of ethanol and warmed to 70° C and stirred at this temperature until no more ammonia evolves. The ethanol solvent is then removed by evaporation under vacuum and the residue poured into 100 ml. of water and extracted three times with ethyl ether. The aqueous solution is acidified to about pH 2 with 5N aqueous hydrochloric acid and then extracted three times with ethyl ether. The ethyl ether extracts are combined and dried over anhydrous magnesium sulfate, filtered and the filtrate evaporated under vacuum to remove the ethyl ether, affording exobicyclo[3.1.0]hex-2-yl acetic acid as a residue. In this preparation 2 ml The ethanol solvent is then removed by evaporation under vacuum the residue poured into 100 ml of water and extracted three times with ethyl ether extracted three times with ethyl ether dried over anhydrous magnesium sulfate filtered the filtrate evaporated under vacuum to remove the ethyl ether

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: Under argon atmosphere, to a solution of sodium metal (70.6 g, 3.07 mol) in absolute ethanol (900 ml) was added ethyl malonate (510 g, 3.18 mol) with stirring. Further, 2-bromohexane (475 g, 2.88 mol) was added dropwise gradually and, after sodium bromide was precipitated, in such a rate that ethanol was slowly refluxed. After addition reflux was continued for 4 hours. After cooling the mixture to room temperature 50% aqueous potassium hydroxide solution (843 g) was added dropwise and the reaction mixture was refluxed for 5 hours. Ethanol was distilled off and the residue was neutralized with concentrated hydrochloric acid (600 ml). The resulting solution was then extracted with ether (one liter×3) and the extracts were dried over anhydrous sodium sulfate. After concentration, the residue was heated at 130° C. for 2 hours and at 180° C. for 2.5 hours. The distillation of the residue under reduced pressure gave dl-3-methylheptanoic acid (310 g, 2.15 mol, 75%, b.p.: 124°-125° C./25 mmHg). after sodium bromide was precipitated in such a rate that ethanol was slowly refluxed After addition reflux was added dropwise the reaction mixture was refluxed for 5 hours Ethanol was distilled off The resulting solution was then extracted with ether (one liter×3) the extracts were dried over anhydrous sodium sulfate After concentration the residue was heated at 130° C. for 2 hours and at 180° C. for 2.5 hours The distillation of the residue under reduced pressure

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

実験手順: In this preparation 2 ml. of 30% aqueous potassium hydroxide is admixed with 0.1 mole of exobicyclo[3.1.0]hex-2-yl acetamide in 20 ml. of ethanol and warmed to 70° C and stirred at this temperature until no more ammonia evolves. The ethanol solvent is then removed by evaporation under vacuum and the residue poured into 100 ml. of water and extracted three times with ethyl ether. The aqueous solution is acidified to about pH 2 with 5N aqueous hydrochloric acid and then extracted three times with ethyl ether. The ethyl ether extracts are combined and dried over anhydrous magnesium sulfate, filtered and the filtrate evaporated under vacuum to remove the ethyl ether, affording exobicyclo[3.1.0]hex-2-yl acetic acid as a residue. In this preparation 2 ml The ethanol solvent is then removed by evaporation under vacuum the residue poured into 100 ml of water and extracted three times with ethyl ether extracted three times with ethyl ether dried over anhydrous magnesium sulfate filtered the filtrate evaporated under vacuum to remove the ethyl ether