undecan-3-ol

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

実験手順: Sodium bicarbonate (8.81 g, 0.105 mol) was added to a solution of 15.0 g (0.075 mol) of 3,3-dimethyl-1,5-dioxaspiro<5.5>undecan-9-ol in 150 ml of acetonitrile. The reaction mixture was charged with 15.0 g of silica gel (MCB 60-200 mesh) and 15.0 g of calcium hypochlorite in sequence. The reaction mixture was stirred at a temperature in the range of 24° C. to 28° C. for about 18 hours and then warmed to 29° C. to 30° C. for 4 hours. The mixture was filtered and evaporated under vacuum. The residue was combined with 135 ml of toluene and 50 ml of water, and the resulting mixture was stirred for 45 minutes. The organic phase was separated, washed with 50 ml of a saturated sodium chloride solution and dried over 10.0 g of anhydrous sodium sulfate. A gas chromatograph of the sample showed 93.6% pure product. The organic phase was concentrated under vacuum to afford 13.97 g of 3,3-dimethyl-1,5-dioxaspiro<5.5>undecan-9-one. warmed to 29° C. to 30° C. for 4 hours The mixture was filtered evaporated under vacuum the resulting mixture was stirred for 45 minutes The organic phase was separated washed with 50 ml of a saturated sodium chloride solution dried over 10.0 g of anhydrous sodium sulfate The organic phase was concentrated under vacuum

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

実験手順: Sodium bicarbonate (8.81 g, 0.105 mol) was added to a solution of 15.0 g (0.075 mol) of 3,3-dimethyl-1,5-dioxaspiro<5.5>undecan-9-ol in 150 ml of acetonitrile. The reaction mixture was charged with 15.0 g of silica gel (MCB 60-200 mesh) and 15.0 g of calcium hypochlorite in sequence. The reaction mixture was stirred at a temperature in the range of 24° C. to 28° C. for about 18 hours and then warmed to 29° C. to 30° C. for 4 hours. The mixture was filtered and evaporated under vacuum. The residue was combined with 135 ml of toluene and 50 ml of water, and the resulting mixture was stirred for 45 minutes. The organic phase was separated, washed with 50 ml of a saturated sodium chloride solution and dried over 10.0 g of anhydrous sodium sulfate. A gas chromatograph of the sample showed 93.6% pure product. The organic phase was concentrated under vacuum to afford 13.97 g of 3,3-dimethyl-1,5-dioxaspiro<5.5>undecan-9-one. warmed to 29° C. to 30° C. for 4 hours The mixture was filtered evaporated under vacuum the resulting mixture was stirred for 45 minutes The organic phase was separated washed with 50 ml of a saturated sodium chloride solution dried over 10.0 g of anhydrous sodium sulfate The organic phase was concentrated under vacuum

反応条件: temp:28.51; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Forty grams (0.2 mol) of 3,3-dimethyl-1,5-dioxaspiro<5.5>undecan-9-ol were dissolved in 400 ml of acetonitrile, and 23.5 g of sodium bicarbonate was added thereto with stirring. Next, 40.0 g of silica gel (MCB Grade 62 60-200 mesh) was added to the mixture, which was followed by the addition of 40.0 g (0.28 mol) of calcium hypochlorite (Fisher Chemical Company) portionwise over a period of 90 seconds. The reaction mixture was stirred at 23.5° C. for one hour and then heated slowly to 28.5° C., and the reaction mixture was stirred overnight. The mixture was filtered into a stirring solution of 8.0 g of sodium bicarbonate in 80 ml of water. The flask was rinsed with 200 ml of toluene and the filtrate was stirred for 90 minutes. The mixture was partially evaporated under reduced pressure and 400 ml of toluene was added thereto. The organic phase was washed with 100 ml of a saturated aqueous sodium chloride solution containing 5.0 g of sodium bicarbonate. The organic phase was dried over anhydrous sodium sulfate. The volatiles were removed under reduced pressure and the residue was held under vacuum for about 60 hours. A total of 38.56 g of 3,3-dimethyl-1,5-dioxaspiro<5.5>-undecan-9-one was obtained having a purity of 93.7% by gas chromatographic analysis (97.2% crude yield). The compound was stored in a solution of 3.55 g of sodium bicarbonate in 200 ml methylene chloride in a sealed bottle. Next, 40.0 g of silica gel (MCB Grade 62 60-200 mesh) was added to the mixture, which The reaction mixture was stirred at 23.5° C. for one hour the reaction mixture was stirred overnight The mixture was filtered into a stirring solution of 8.0 g of sodium bicarbonate in 80 ml of water The flask was rinsed with 200 ml of toluene the filtrate was stirred for 90 minutes The mixture was partially evaporated under reduced pressure and 400 ml of toluene was added The organic phase was washed with 100 ml of a saturated aqueous sodium chloride solution containing 5.0 g of sodium bicarbonate The organic phase was dried over anhydrous sodium sulfate The volatiles were removed under reduced pressure

反応条件: temp:28.51; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Forty grams (0.2 mol) of 3,3-dimethyl-1,5-dioxaspiro<5.5>undecan-9-ol were dissolved in 400 ml of acetonitrile, and 23.5 g of sodium bicarbonate was added thereto with stirring. Next, 40.0 g of silica gel (MCB Grade 62 60-200 mesh) was added to the mixture, which was followed by the addition of 40.0 g (0.28 mol) of calcium hypochlorite (Fisher Chemical Company) portionwise over a period of 90 seconds. The reaction mixture was stirred at 23.5° C. for one hour and then heated slowly to 28.5° C., and the reaction mixture was stirred overnight. The mixture was filtered into a stirring solution of 8.0 g of sodium bicarbonate in 80 ml of water. The flask was rinsed with 200 ml of toluene and the filtrate was stirred for 90 minutes. The mixture was partially evaporated under reduced pressure and 400 ml of toluene was added thereto. The organic phase was washed with 100 ml of a saturated aqueous sodium chloride solution containing 5.0 g of sodium bicarbonate. The organic phase was dried over anhydrous sodium sulfate. The volatiles were removed under reduced pressure and the residue was held under vacuum for about 60 hours. A total of 38.56 g of 3,3-dimethyl-1,5-dioxaspiro<5.5>-undecan-9-one was obtained having a purity of 93.7% by gas chromatographic analysis (97.2% crude yield). The compound was stored in a solution of 3.55 g of sodium bicarbonate in 200 ml methylene chloride in a sealed bottle. Next, 40.0 g of silica gel (MCB Grade 62 60-200 mesh) was added to the mixture, which The reaction mixture was stirred at 23.5° C. for one hour the reaction mixture was stirred overnight The mixture was filtered into a stirring solution of 8.0 g of sodium bicarbonate in 80 ml of water The flask was rinsed with 200 ml of toluene the filtrate was stirred for 90 minutes The mixture was partially evaporated under reduced pressure and 400 ml of toluene was added The organic phase was washed with 100 ml of a saturated aqueous sodium chloride solution containing 5.0 g of sodium bicarbonate The organic phase was dried over anhydrous sodium sulfate The volatiles were removed under reduced pressure

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

実験手順: Sodium bicarbonate (8.81 g, 0.105 mol) was added to a solution of 15.0 g (0.075 mol) of 3,3-dimethyl-1,5-dioxaspiro<5.5>undecan-9-ol in 150 ml of acetonitrile. The reaction mixture was charged with 15.0 g of silica gel (MCB 60-200 mesh) and 15.0 g of calcium hypochlorite in sequence. The reaction mixture was stirred at a temperature in the range of 24° C. to 28° C. for about 18 hours and then warmed to 29° C. to 30° C. for 4 hours. The mixture was filtered and evaporated under vacuum. The residue was combined with 135 ml of toluene and 50 ml of water, and the resulting mixture was stirred for 45 minutes. The organic phase was separated, washed with 50 ml of a saturated sodium chloride solution and dried over 10.0 g of anhydrous sodium sulfate. A gas chromatograph of the sample showed 93.6% pure product. The organic phase was concentrated under vacuum to afford 13.97 g of 3,3-dimethyl-1,5-dioxaspiro<5.5>undecan-9-one. warmed to 29° C. to 30° C. for 4 hours The mixture was filtered evaporated under vacuum the resulting mixture was stirred for 45 minutes The organic phase was separated washed with 50 ml of a saturated sodium chloride solution dried over 10.0 g of anhydrous sodium sulfate The organic phase was concentrated under vacuum

反応条件: temp:28.51; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Forty grams (0.2 mol) of 3,3-dimethyl-1,5-dioxaspiro<5.5>undecan-9-ol were dissolved in 400 ml of acetonitrile, and 23.5 g of sodium bicarbonate was added thereto with stirring. Next, 40.0 g of silica gel (MCB Grade 62 60-200 mesh) was added to the mixture, which was followed by the addition of 40.0 g (0.28 mol) of calcium hypochlorite (Fisher Chemical Company) portionwise over a period of 90 seconds. The reaction mixture was stirred at 23.5° C. for one hour and then heated slowly to 28.5° C., and the reaction mixture was stirred overnight. The mixture was filtered into a stirring solution of 8.0 g of sodium bicarbonate in 80 ml of water. The flask was rinsed with 200 ml of toluene and the filtrate was stirred for 90 minutes. The mixture was partially evaporated under reduced pressure and 400 ml of toluene was added thereto. The organic phase was washed with 100 ml of a saturated aqueous sodium chloride solution containing 5.0 g of sodium bicarbonate. The organic phase was dried over anhydrous sodium sulfate. The volatiles were removed under reduced pressure and the residue was held under vacuum for about 60 hours. A total of 38.56 g of 3,3-dimethyl-1,5-dioxaspiro<5.5>-undecan-9-one was obtained having a purity of 93.7% by gas chromatographic analysis (97.2% crude yield). The compound was stored in a solution of 3.55 g of sodium bicarbonate in 200 ml methylene chloride in a sealed bottle. Next, 40.0 g of silica gel (MCB Grade 62 60-200 mesh) was added to the mixture, which The reaction mixture was stirred at 23.5° C. for one hour the reaction mixture was stirred overnight The mixture was filtered into a stirring solution of 8.0 g of sodium bicarbonate in 80 ml of water The flask was rinsed with 200 ml of toluene the filtrate was stirred for 90 minutes The mixture was partially evaporated under reduced pressure and 400 ml of toluene was added The organic phase was washed with 100 ml of a saturated aqueous sodium chloride solution containing 5.0 g of sodium bicarbonate The organic phase was dried over anhydrous sodium sulfate The volatiles were removed under reduced pressure

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

実験手順: Sodium bicarbonate (8.81 g, 0.105 mol) was added to a solution of 15.0 g (0.075 mol) of 3,3-dimethyl-1,5-dioxaspiro<5.5>undecan-9-ol in 150 ml of acetonitrile. The reaction mixture was charged with 15.0 g of silica gel (MCB 60-200 mesh) and 15.0 g of calcium hypochlorite in sequence. The reaction mixture was stirred at a temperature in the range of 24° C. to 28° C. for about 18 hours and then warmed to 29° C. to 30° C. for 4 hours. The mixture was filtered and evaporated under vacuum. The residue was combined with 135 ml of toluene and 50 ml of water, and the resulting mixture was stirred for 45 minutes. The organic phase was separated, washed with 50 ml of a saturated sodium chloride solution and dried over 10.0 g of anhydrous sodium sulfate. A gas chromatograph of the sample showed 93.6% pure product. The organic phase was concentrated under vacuum to afford 13.97 g of 3,3-dimethyl-1,5-dioxaspiro<5.5>undecan-9-one. warmed to 29° C. to 30° C. for 4 hours The mixture was filtered evaporated under vacuum the resulting mixture was stirred for 45 minutes The organic phase was separated washed with 50 ml of a saturated sodium chloride solution dried over 10.0 g of anhydrous sodium sulfate The organic phase was concentrated under vacuum

反応条件: temp:28.51; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Forty grams (0.2 mol) of 3,3-dimethyl-1,5-dioxaspiro<5.5>undecan-9-ol were dissolved in 400 ml of acetonitrile, and 23.5 g of sodium bicarbonate was added thereto with stirring. Next, 40.0 g of silica gel (MCB Grade 62 60-200 mesh) was added to the mixture, which was followed by the addition of 40.0 g (0.28 mol) of calcium hypochlorite (Fisher Chemical Company) portion-wise over a period of 90 seconds. The reaction mixture was stirred at 23.5° C. for one hour and then heated slowly to 28.5° C., and the reaction mixture was stirred overnight. The mixture was filtered into a stirring solution of 8.0 g of sodium bicarbonate in 80 ml of water. The flask was rinsed with 200 ml of toluene and the filtrate was stirred for 90 minutes. The mixture was partially evaporated under reduced pressure and 400 ml of toluene was added thereto. The organic phase was washed with 100 ml of a saturated aqueous sodium chloride solution containing 5.0 g of sodium bicarbonate. the organic phase was dried over anhydrous sodium sulfate. The volatiles were removed under reduced pressure and the residue was held under vacuum for about 60 hours. A total of 38.56 g of 3,3-dimethyl-1,5-dioxaspiro<5.5>-undecan-9-one was obtained having a purity of 93.7% by gas chromatographic analysis (97.2% crude yield). The compound was stored in a solution of 3.55 g of sodium bicarbonate in 200 ml methylene chloride in a sealed bottle. Next, 40.0 g of silica gel (MCB Grade 62 60-200 mesh) was added to the mixture, which The reaction mixture was stirred at 23.5° C. for one hour the reaction mixture was stirred overnight The mixture was filtered into a stirring solution of 8.0 g of sodium bicarbonate in 80 ml of water The flask was rinsed with 200 ml of toluene the filtrate was stirred for 90 minutes The mixture was partially evaporated under reduced pressure and 400 ml of toluene was added The organic phase was washed with 100 ml of a saturated aqueous sodium chloride solution containing 5.0 g of sodium bicarbonate the organic phase was dried over anhydrous sodium sulfate The volatiles were removed under reduced pressure

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

実験手順: Sodium bicarbonate (8.81 g, 0.105 mol) was added to a solution of 15.0 g (0.075 mol) of 3,3-dimethyl-1,5-dioxaspiro<5.5>undecan-9-ol in 150 ml of acetonitrile. The reaction mixture was charged with 15.0 g of silica gel (MCB 60-200 mesh) and 15.0 g of calcium hypochlorite in sequence. The reaction mixture was stirred at a temperature in the range of 24° C. to 28° C. for about 18 hours and then warmed to 29° C. to 30° C. for 4 hours. The mixture was filtered and evaporated under vacuum. The residue was combined with 135 ml of toluene and 50 ml of water, and the resulting mixture was stirred for 45 minutes. The organic phase was separated, washed with 50 ml of a saturated sodium chloride solution and dried over 10.0 g of anhydrous sodium sulfate. A gas chromatograph of the sample showed 93.6% pure product. The organic phase was concentrated under vacuum to afford 13.97 g of 3,3-dimethyl-1,5-dioxaspiro<5.5>undecan-9-one. warmed to 29° C. to 30° C. for 4 hours The mixture was filtered evaporated under vacuum the resulting mixture was stirred for 45 minutes The organic phase was separated washed with 50 ml of a saturated sodium chloride solution dried over 10.0 g of anhydrous sodium sulfate The organic phase was concentrated under vacuum

反応条件: temp:28.51; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Forty grams (0.2 mol) of 3,3-dimethyl-1,5-dioxaspiro<5.5>undecan-9-ol were dissolved in 400 ml of acetonitrile, and 23.5 g of sodium bicarbonate was added thereto with stirring. Next, 40.0 g of silica gel (MCB Grade 62 60-200 mesh) was added to the mixture, which was followed by the addition of 40.0 g (0.28 mol) of calcium hypochlorite (Fisher Chemical Company) portionwise over a period of 90 seconds. The reaction mixture was stirred at 23.5° C. for one hour and then heated slowly to 28.5° C., and the reaction mixture was stirred overnight. The mixture was filtered into a stirring solution of 8.0 g of sodium bicarbonate in 80 ml of water. The flask was rinsed with 200 ml of toluene and the filtrate was stirred for 90 minutes. The mixture was partially evaporated under reduced pressure and 400 ml of toluene was added thereto. The organic phase was washed with 100 ml of a saturated aqueous sodium chloride solution containing 5.0 g of sodium bicarbonate. The organic phase was dried over anhydrous sodium sulfate. The volatiles were removed under reduced pressure and the residue was held under vacuum for about 60 hours. A total of 38.56 g of 3,3-dimethyl-1,5-dioxaspiro<5.5>-undecan-9-one was obtained having a purity of 93.7% by gas chromatographic analysis (97.2% crude yield). The compound was stored in a solution of 3.55 g of sodium bicarbonate in 200 ml methylene chloride in a sealed bottle. Next, 40.0 g of silica gel (MCB Grade 62 60-200 mesh) was added to the mixture, which The reaction mixture was stirred at 23.5° C. for one hour the reaction mixture was stirred overnight The mixture was filtered into a stirring solution of 8.0 g of sodium bicarbonate in 80 ml of water The flask was rinsed with 200 ml of toluene the filtrate was stirred for 90 minutes The mixture was partially evaporated under reduced pressure and 400 ml of toluene was added The organic phase was washed with 100 ml of a saturated aqueous sodium chloride solution containing 5.0 g of sodium bicarbonate The organic phase was dried over anhydrous sodium sulfate The volatiles were removed under reduced pressure